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molecular formula C25H24N4O5 B105213 1-(4-Methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid CAS No. 503614-92-4

1-(4-Methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid

Cat. No. B105213
M. Wt: 460.5 g/mol
InChI Key: PPUHOTDYJQGTAE-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US07153960B2

Procedure details

Method A. A suspension of 1-(4-methoxy-phenyl)-7-oxo-6-[4-(2-oxo-piperidin-1-yl)-phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid (61, 1.5 g, 3.3 mmol) in EtOAc (20 mL) was treated with triethylamine (TEA, 433 mg, 0.60 mL, 4.3 mmol, 1.3 equiv) at room temperature, and the resulting reaction mixture was treated dropwise with iso-butyl chloroformate (587 mg, 0.55 mL, 4.3 mmol, 1.3 equiv) at room temperature. The resulting reaction mixture was subsequently stirred at room temperature for an additional 30 min. When TLC and HPLC showed the mixed anhydride formation reaction was complete, the reaction mixture was poured into a cold (0–5° C.) ammonium hydroxide solution (NH4OH, 28% aqueous solution, 25 mL) with good stirring. The resulting mixture was stirred at room temperature for an additional 4 h. The solids were collected by filtration, washed with a mixture of methanol and water (1:1 v/v, 2×20 mL), and dried in vacuo at 40–45° C. for 12 h to afford the crude desired 1-(4-methoxy-phenyl)-7-oxo-6-[4-(2-oxo-piperidin-1-yl)-phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid amide (62, 1.06 g, 1.52 g theoretical, 70%) as off-white crystals. For 62, CIMS m/z 460 (M++H, C25H25N5O4).
Name
Quantity
20 mL
Type
solvent
Reaction Step One
Quantity
0.6 mL
Type
reactant
Reaction Step Two
Quantity
0.55 mL
Type
reactant
Reaction Step Three
[Compound]
Name
anhydride
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
25 mL
Type
reactant
Reaction Step Five

Identifiers

REACTION_CXSMILES
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:31])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([N:24]5[CH2:29][CH2:28][CH2:27][CH2:26][C:25]5=[O:30])=[CH:20][CH:19]=4)[CH2:16][CH2:17][C:12]=3[C:11]([C:32]([OH:34])=O)=[N:10]2)=[CH:5][CH:4]=1.C([N:37](CC)CC)C.ClC(OCC(C)C)=O.[OH-].[NH4+]>CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:31])[N:15]([C:18]4[CH:19]=[CH:20][C:21]([N:24]5[CH2:29][CH2:28][CH2:27][CH2:26][C:25]5=[O:30])=[CH:22][CH:23]=4)[CH2:16][CH2:17][C:12]=3[C:11]([C:32]([NH2:37])=[O:34])=[N:10]2)=[CH:5][CH:4]=1 |f:3.4|

Inputs

Step One
Name
Quantity
1.5 g
Type
reactant
Smiles
COC1=CC=C(C=C1)N1N=C(C2=C1C(N(CC2)C2=CC=C(C=C2)N2C(CCCC2)=O)=O)C(=O)O
Name
Quantity
20 mL
Type
solvent
Smiles
CCOC(=O)C
Step Two
Name
Quantity
0.6 mL
Type
reactant
Smiles
C(C)N(CC)CC
Step Three
Name
Quantity
0.55 mL
Type
reactant
Smiles
ClC(=O)OCC(C)C
Step Four
Name
anhydride
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Five
Name
Quantity
25 mL
Type
reactant
Smiles
[OH-].[NH4+]

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
was subsequently stirred at room temperature for an additional 30 min
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
the resulting reaction mixture
CUSTOM
Type
CUSTOM
Details
The resulting reaction mixture
STIRRING
Type
STIRRING
Details
The resulting mixture was stirred at room temperature for an additional 4 h
Duration
4 h
FILTRATION
Type
FILTRATION
Details
The solids were collected by filtration
WASH
Type
WASH
Details
washed with a mixture of methanol and water (1:1 v/v, 2×20 mL)
CUSTOM
Type
CUSTOM
Details
dried in vacuo at 40–45° C. for 12 h
Duration
12 h

Outcomes

Product
Details
Reaction Time
30 min
Name
Type
product
Smiles
COC1=CC=C(C=C1)N1N=C(C2=C1C(N(CC2)C2=CC=C(C=C2)N2C(CCCC2)=O)=O)C(=O)N
Measurements
Type Value Analysis
AMOUNT: MASS 1.06 g
YIELD: PERCENTYIELD 70%
YIELD: CALCULATEDPERCENTYIELD 69.9%

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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