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molecular formula C28H33N7O2 B2766964 Osimertinib D6 CAS No. 1638281-44-3

Osimertinib D6

Cat. No. B2766964
M. Wt: 505.656
InChI Key: DUYJMQONPNNFPI-XERRXZQWSA-N
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Patent
US08946235B2

Procedure details

To a stirred solution of 3-chloro-N-[2-[2-dimethylaminoethyl(methyl)amino]-4-methoxy-5-[[4-(1-methylindol-3-yl)pyrimidin-2-yl]amino]phenyl]propanamide (Intermediate 174, 31.5 g, 58.76 mmol) in acetonitrile (310 mL) was added triethylamine (17.84 g, 176.28 mmol) at r.t. The resulting mixture was heated to 80° C. for 6 h then cooled to r.t. Water (130 mL) was then added and the mixture stirred for 12 h. The mixture was then filtered, washed with a mixture of water and acetonitrile (160 mL, 1:1) and dried at 50° C. for overnight to give the title compound (19.2 g, 94%) as a solid form identified herein as polymorphic form D. 1H NMR: 2.69 (3H, s), 2.83 (6H, d), 3.35 (4H, s), 3.84 (3H, s), 3.91 (3H, s), 5.75 (1H, d), 6.28 (1H, d), 6.67 (1H, dd), 7.05-7.23 (2H, m), 7.29 (1H, t), 7.43 (1H, d), 7.56 (1H, d), 8.21 (2H, s), 8.81 (1H, s), 9.47 (1H, s), 9.52 (1H, s), m/z: ES+ MH+ 500.26.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
17.84 g
Type
reactant
Reaction Step One
Quantity
310 mL
Type
solvent
Reaction Step One
Name
Quantity
130 mL
Type
reactant
Reaction Step Two
Yield
94%

Identifiers

REACTION_CXSMILES
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([NH:13][C:14]2[N:19]=[C:18]([C:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]([CH3:29])[CH:21]=3)[CH:17]=[CH:16][N:15]=2)[C:10]([O:30][CH3:31])=[CH:9][C:8]=1[N:32]([CH2:34][CH2:35][N:36]([CH3:38])[CH3:37])[CH3:33])=[O:5].C(N(CC)CC)C.O>C(#N)C>[CH3:38][N:36]([CH3:37])[CH2:35][CH2:34][N:32]([CH3:33])[C:8]1[CH:9]=[C:10]([O:30][CH3:31])[C:11]([NH:13][C:14]2[N:19]=[C:18]([C:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]([CH3:29])[CH:21]=3)[CH:17]=[CH:16][N:15]=2)=[CH:12][C:7]=1[NH:6][C:4](=[O:5])[CH:3]=[CH2:2]

Inputs

Step One
Name
Quantity
31.5 g
Type
reactant
Smiles
ClCCC(=O)NC1=C(C=C(C(=C1)NC1=NC=CC(=N1)C1=CN(C2=CC=CC=C12)C)OC)N(C)CCN(C)C
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClCCC(=O)NC1=C(C=C(C(=C1)NC1=NC=CC(=N1)C1=CN(C2=CC=CC=C12)C)OC)N(C)CCN(C)C
Name
Quantity
17.84 g
Type
reactant
Smiles
C(C)N(CC)CC
Name
Quantity
310 mL
Type
solvent
Smiles
C(C)#N
Step Two
Name
Quantity
130 mL
Type
reactant
Smiles
O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
80 °C
Stirring
Type
CUSTOM
Details
the mixture stirred for 12 h
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
then cooled to r.t
FILTRATION
Type
FILTRATION
Details
The mixture was then filtered
WASH
Type
WASH
Details
washed with a mixture of water and acetonitrile (160 mL, 1:1)
CUSTOM
Type
CUSTOM
Details
dried at 50° C. for overnight
Duration
8 (± 8) h

Outcomes

Product
Details
Reaction Time
12 h
Name
Type
product
Smiles
CN(CCN(C1=C(C=C(C(=C1)OC)NC1=NC=CC(=N1)C1=CN(C2=CC=CC=C12)C)NC(C=C)=O)C)C
Measurements
Type Value Analysis
AMOUNT: MASS 19.2 g
YIELD: PERCENTYIELD 94%
YIELD: CALCULATEDPERCENTYIELD 65.4%

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
US08946235B2

Procedure details

To a stirred solution of 3-chloro-N-[2-[2-dimethylaminoethyl(methyl)amino]-4-methoxy-5-[[4-(1-methylindol-3-yl)pyrimidin-2-yl]amino]phenyl]propanamide (Intermediate 174, 31.5 g, 58.76 mmol) in acetonitrile (310 mL) was added triethylamine (17.84 g, 176.28 mmol) at r.t. The resulting mixture was heated to 80° C. for 6 h then cooled to r.t. Water (130 mL) was then added and the mixture stirred for 12 h. The mixture was then filtered, washed with a mixture of water and acetonitrile (160 mL, 1:1) and dried at 50° C. for overnight to give the title compound (19.2 g, 94%) as a solid form identified herein as polymorphic form D. 1H NMR: 2.69 (3H, s), 2.83 (6H, d), 3.35 (4H, s), 3.84 (3H, s), 3.91 (3H, s), 5.75 (1H, d), 6.28 (1H, d), 6.67 (1H, dd), 7.05-7.23 (2H, m), 7.29 (1H, t), 7.43 (1H, d), 7.56 (1H, d), 8.21 (2H, s), 8.81 (1H, s), 9.47 (1H, s), 9.52 (1H, s), m/z: ES+ MH+ 500.26.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
17.84 g
Type
reactant
Reaction Step One
Quantity
310 mL
Type
solvent
Reaction Step One
Name
Quantity
130 mL
Type
reactant
Reaction Step Two
Yield
94%

Identifiers

REACTION_CXSMILES
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([NH:13][C:14]2[N:19]=[C:18]([C:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]([CH3:29])[CH:21]=3)[CH:17]=[CH:16][N:15]=2)[C:10]([O:30][CH3:31])=[CH:9][C:8]=1[N:32]([CH2:34][CH2:35][N:36]([CH3:38])[CH3:37])[CH3:33])=[O:5].C(N(CC)CC)C.O>C(#N)C>[CH3:38][N:36]([CH3:37])[CH2:35][CH2:34][N:32]([CH3:33])[C:8]1[CH:9]=[C:10]([O:30][CH3:31])[C:11]([NH:13][C:14]2[N:19]=[C:18]([C:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]([CH3:29])[CH:21]=3)[CH:17]=[CH:16][N:15]=2)=[CH:12][C:7]=1[NH:6][C:4](=[O:5])[CH:3]=[CH2:2]

Inputs

Step One
Name
Quantity
31.5 g
Type
reactant
Smiles
ClCCC(=O)NC1=C(C=C(C(=C1)NC1=NC=CC(=N1)C1=CN(C2=CC=CC=C12)C)OC)N(C)CCN(C)C
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClCCC(=O)NC1=C(C=C(C(=C1)NC1=NC=CC(=N1)C1=CN(C2=CC=CC=C12)C)OC)N(C)CCN(C)C
Name
Quantity
17.84 g
Type
reactant
Smiles
C(C)N(CC)CC
Name
Quantity
310 mL
Type
solvent
Smiles
C(C)#N
Step Two
Name
Quantity
130 mL
Type
reactant
Smiles
O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
80 °C
Stirring
Type
CUSTOM
Details
the mixture stirred for 12 h
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
then cooled to r.t
FILTRATION
Type
FILTRATION
Details
The mixture was then filtered
WASH
Type
WASH
Details
washed with a mixture of water and acetonitrile (160 mL, 1:1)
CUSTOM
Type
CUSTOM
Details
dried at 50° C. for overnight
Duration
8 (± 8) h

Outcomes

Product
Details
Reaction Time
12 h
Name
Type
product
Smiles
CN(CCN(C1=C(C=C(C(=C1)OC)NC1=NC=CC(=N1)C1=CN(C2=CC=CC=C12)C)NC(C=C)=O)C)C
Measurements
Type Value Analysis
AMOUNT: MASS 19.2 g
YIELD: PERCENTYIELD 94%
YIELD: CALCULATEDPERCENTYIELD 65.4%

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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