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molecular formula C17H19N3O3S B000731 Omeprazole CAS No. 73590-58-6

Omeprazole

Cat. No. B000731
M. Wt: 345.4 g/mol
InChI Key: SUBDBMMJDZJVOS-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US06706737B2

Procedure details

To a 50 mL beaker was added about 1 g of (5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole to 30 mL of dimethylformamide (DMF) containing 1 mL of ammonium hydroxide. Additional (5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole was added to the resulting solution until a suspension of the material was formed. The solution was stirred for approximately 10 minutes, and then filtered through a 0.45 μm Poly(tetrafluoroethylene) (PTFE) or Nylon filter. The resulting saturated solution was placed in a shallow petri dish, covered and stored under ambient conditions (approximately 25° C.) and a humidity range of 0 to 50 percent until crystals formed (between 1-4 days). The identity of the title compound is confirmed by single crystal x-ray diffraction and/or Raman spectroscopy. The resulting material was shown to contain between about 96 and 98 percent (w/w) of the 6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole and between about 2 and 4 percent (w/w) of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole.
Name
(5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole
Quantity
1 g
Type
reactant
Reaction Step One
Quantity
30 mL
Type
solvent
Reaction Step One
Quantity
1 mL
Type
reactant
Reaction Step Two
Name
(5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([S@:11]([CH2:13][C:14]3[C:19]([CH3:20])=[C:18]([O:21][CH3:22])[C:17]([CH3:23])=[CH:16][N:15]=3)=[O:12])[NH:8][C:7]=2[CH:24]=1.[OH-].[NH4+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([S:11]([CH2:13][C:14]3[C:19]([CH3:20])=[C:18]([O:21][CH3:22])[C:17]([CH3:23])=[CH:16][N:15]=3)=[O:12])[NH:8][C:7]=2[CH:24]=1 |f:1.2|

Inputs

Step One
Name
(5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole
Quantity
1 g
Type
reactant
Smiles
COC=1C=CC2=C(NC(=N2)[S@@](=O)CC2=NC=C(C(=C2C)OC)C)C1
Name
Quantity
30 mL
Type
solvent
Smiles
CN(C=O)C
Step Two
Name
Quantity
1 mL
Type
reactant
Smiles
[OH-].[NH4+]
Step Three
Name
(5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole
Quantity
0 (± 1) mol
Type
reactant
Smiles
COC=1C=CC2=C(NC(=N2)[S@@](=O)CC2=NC=C(C(=C2C)OC)C)C1

Conditions

Stirring
Type
CUSTOM
Details
The solution was stirred for approximately 10 minutes
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
was formed
FILTRATION
Type
FILTRATION
Details
filtered through a 0.45 μm Poly(tetrafluoroethylene) (PTFE) or Nylon
FILTRATION
Type
FILTRATION
Details
filter
CUSTOM
Type
CUSTOM
Details
stored under ambient conditions (approximately 25° C.)
CUSTOM
Type
CUSTOM
Details
a humidity range of 0 to 50 percent until crystals formed (between 1-4 days)
Duration
2.5 (± 1.5) d

Outcomes

Product
Details
Reaction Time
10 min
Name
Type
product
Smiles
COC=1C=CC2=C(NC(=N2)S(=O)CC2=NC=C(C(=C2C)OC)C)C1

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US06706737B2

Procedure details

To a 50 mL beaker was added about 1 g of (5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole to 30 mL of dimethylformamide (DMF) containing 1 mL of ammonium hydroxide. Additional (5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole was added to the resulting solution until a suspension of the material was formed. The solution was stirred for approximately 10 minutes, and then filtered through a 0.45 μm Poly(tetrafluoroethylene) (PTFE) or Nylon filter. The resulting saturated solution was placed in a shallow petri dish, covered and stored under ambient conditions (approximately 25° C.) and a humidity range of 0 to 50 percent until crystals formed (between 1-4 days). The identity of the title compound is confirmed by single crystal x-ray diffraction and/or Raman spectroscopy. The resulting material was shown to contain between about 96 and 98 percent (w/w) of the 6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole and between about 2 and 4 percent (w/w) of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole.
Name
(5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole
Quantity
1 g
Type
reactant
Reaction Step One
Quantity
30 mL
Type
solvent
Reaction Step One
Quantity
1 mL
Type
reactant
Reaction Step Two
Name
(5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([S@:11]([CH2:13][C:14]3[C:19]([CH3:20])=[C:18]([O:21][CH3:22])[C:17]([CH3:23])=[CH:16][N:15]=3)=[O:12])[NH:8][C:7]=2[CH:24]=1.[OH-].[NH4+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([S:11]([CH2:13][C:14]3[C:19]([CH3:20])=[C:18]([O:21][CH3:22])[C:17]([CH3:23])=[CH:16][N:15]=3)=[O:12])[NH:8][C:7]=2[CH:24]=1 |f:1.2|

Inputs

Step One
Name
(5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole
Quantity
1 g
Type
reactant
Smiles
COC=1C=CC2=C(NC(=N2)[S@@](=O)CC2=NC=C(C(=C2C)OC)C)C1
Name
Quantity
30 mL
Type
solvent
Smiles
CN(C=O)C
Step Two
Name
Quantity
1 mL
Type
reactant
Smiles
[OH-].[NH4+]
Step Three
Name
(5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole
Quantity
0 (± 1) mol
Type
reactant
Smiles
COC=1C=CC2=C(NC(=N2)[S@@](=O)CC2=NC=C(C(=C2C)OC)C)C1

Conditions

Stirring
Type
CUSTOM
Details
The solution was stirred for approximately 10 minutes
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
was formed
FILTRATION
Type
FILTRATION
Details
filtered through a 0.45 μm Poly(tetrafluoroethylene) (PTFE) or Nylon
FILTRATION
Type
FILTRATION
Details
filter
CUSTOM
Type
CUSTOM
Details
stored under ambient conditions (approximately 25° C.)
CUSTOM
Type
CUSTOM
Details
a humidity range of 0 to 50 percent until crystals formed (between 1-4 days)
Duration
2.5 (± 1.5) d

Outcomes

Product
Details
Reaction Time
10 min
Name
Type
product
Smiles
COC=1C=CC2=C(NC(=N2)S(=O)CC2=NC=C(C(=C2C)OC)C)C1

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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