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molecular formula C22H24ClFN4O3 B563487 Gefitinib-d3 CAS No. 1173976-40-3

Gefitinib-d3

Cat. No. B563487
M. Wt: 449.926
InChI Key: XGALLCVXEZPNRQ-FIBGUPNXSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US08350029B2

Procedure details

Methanol (1200 ml) and 6-(3-morpholino propoxy)-7-methoxy-4-chloro quinazoline (200 gm) were stirred for 15 minutes at 25-30° C., then a solution of 4-fluoro-3-chloroaniline in methanol (213 gm in 400 ml) was charged and refluxed for 6 hours. The reaction mass was cooled to 15-20° C., hydrochloric acid (40 ml) was added drop wise, and stirred at 5-10° C. for 30 minutes. The solid obtained was filtered and washed with chilled methanol (150 ml). The solid was dissolved in a mixture of toluene (30 volume) and methanol (5 volume), the reaction mass was concentrated to half the volume and cooled to 5-10° C. The solid obtained was filtered, washed with toluene (200 ml) and dried at 45-50° C. to yield the title compound (183 gm, 70% yield).
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
400 mL
Type
solvent
Reaction Step One
Quantity
40 mL
Type
reactant
Reaction Step Two
Quantity
200 g
Type
reactant
Reaction Step Three
Quantity
1200 mL
Type
solvent
Reaction Step Three
Yield
70%

Identifiers

REACTION_CXSMILES
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][C:20]=2[O:21][CH3:22])[N:17]=[CH:16][N:15]=[C:14]3Cl)[CH2:3][CH2:2]1.[F:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][C:26]=1[Cl:32].Cl>CO>[Cl:32][C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][C:25]=1[F:24])[NH:29][C:14]1[C:13]2[C:18](=[CH:19][C:20]([O:21][CH3:22])=[C:11]([O:10][CH2:9][CH2:8][CH2:7][N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[CH:12]=2)[N:17]=[CH:16][N:15]=1

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
FC1=C(C=C(N)C=C1)Cl
Name
Quantity
400 mL
Type
solvent
Smiles
CO
Step Two
Name
Quantity
40 mL
Type
reactant
Smiles
Cl
Step Three
Name
Quantity
200 g
Type
reactant
Smiles
O1CCN(CC1)CCCOC=1C=C2C(=NC=NC2=CC1OC)Cl
Name
Quantity
1200 mL
Type
solvent
Smiles
CO

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
17.5 (± 2.5) °C
Stirring
Type
CUSTOM
Details
stirred at 5-10° C. for 30 minutes
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
refluxed for 6 hours
Duration
6 h
CUSTOM
Type
CUSTOM
Details
The solid obtained
FILTRATION
Type
FILTRATION
Details
was filtered
WASH
Type
WASH
Details
washed with chilled methanol (150 ml)
DISSOLUTION
Type
DISSOLUTION
Details
The solid was dissolved in a mixture of toluene (30 volume) and methanol (5 volume)
CONCENTRATION
Type
CONCENTRATION
Details
the reaction mass was concentrated to half the volume
TEMPERATURE
Type
TEMPERATURE
Details
cooled to 5-10° C
CUSTOM
Type
CUSTOM
Details
The solid obtained
FILTRATION
Type
FILTRATION
Details
was filtered
WASH
Type
WASH
Details
washed with toluene (200 ml)
CUSTOM
Type
CUSTOM
Details
dried at 45-50° C.

Outcomes

Product
Details
Reaction Time
30 min
Name
Type
product
Smiles
ClC=1C=C(NC2=NC=NC3=CC(=C(C=C23)OCCCN2CCOCC2)OC)C=CC1F
Measurements
Type Value Analysis
AMOUNT: MASS 183 g
YIELD: PERCENTYIELD 70%

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
US08350029B2

Procedure details

Methanol (1200 ml) and 6-(3-morpholino propoxy)-7-methoxy-4-chloro quinazoline (200 gm) were stirred for 15 minutes at 25-30° C., then a solution of 4-fluoro-3-chloroaniline in methanol (213 gm in 400 ml) was charged and refluxed for 6 hours. The reaction mass was cooled to 15-20° C., hydrochloric acid (40 ml) was added drop wise, and stirred at 5-10° C. for 30 minutes. The solid obtained was filtered and washed with chilled methanol (150 ml). The solid was dissolved in a mixture of toluene (30 volume) and methanol (5 volume), the reaction mass was concentrated to half the volume and cooled to 5-10° C. The solid obtained was filtered, washed with toluene (200 ml) and dried at 45-50° C. to yield the title compound (183 gm, 70% yield).
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
400 mL
Type
solvent
Reaction Step One
Quantity
40 mL
Type
reactant
Reaction Step Two
Quantity
200 g
Type
reactant
Reaction Step Three
Quantity
1200 mL
Type
solvent
Reaction Step Three
Yield
70%

Identifiers

REACTION_CXSMILES
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][C:20]=2[O:21][CH3:22])[N:17]=[CH:16][N:15]=[C:14]3Cl)[CH2:3][CH2:2]1.[F:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][C:26]=1[Cl:32].Cl>CO>[Cl:32][C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][C:25]=1[F:24])[NH:29][C:14]1[C:13]2[C:18](=[CH:19][C:20]([O:21][CH3:22])=[C:11]([O:10][CH2:9][CH2:8][CH2:7][N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[CH:12]=2)[N:17]=[CH:16][N:15]=1

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
FC1=C(C=C(N)C=C1)Cl
Name
Quantity
400 mL
Type
solvent
Smiles
CO
Step Two
Name
Quantity
40 mL
Type
reactant
Smiles
Cl
Step Three
Name
Quantity
200 g
Type
reactant
Smiles
O1CCN(CC1)CCCOC=1C=C2C(=NC=NC2=CC1OC)Cl
Name
Quantity
1200 mL
Type
solvent
Smiles
CO

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
17.5 (± 2.5) °C
Stirring
Type
CUSTOM
Details
stirred at 5-10° C. for 30 minutes
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
refluxed for 6 hours
Duration
6 h
CUSTOM
Type
CUSTOM
Details
The solid obtained
FILTRATION
Type
FILTRATION
Details
was filtered
WASH
Type
WASH
Details
washed with chilled methanol (150 ml)
DISSOLUTION
Type
DISSOLUTION
Details
The solid was dissolved in a mixture of toluene (30 volume) and methanol (5 volume)
CONCENTRATION
Type
CONCENTRATION
Details
the reaction mass was concentrated to half the volume
TEMPERATURE
Type
TEMPERATURE
Details
cooled to 5-10° C
CUSTOM
Type
CUSTOM
Details
The solid obtained
FILTRATION
Type
FILTRATION
Details
was filtered
WASH
Type
WASH
Details
washed with toluene (200 ml)
CUSTOM
Type
CUSTOM
Details
dried at 45-50° C.

Outcomes

Product
Details
Reaction Time
30 min
Name
Type
product
Smiles
ClC=1C=C(NC2=NC=NC3=CC(=C(C=C23)OCCCN2CCOCC2)OC)C=CC1F
Measurements
Type Value Analysis
AMOUNT: MASS 183 g
YIELD: PERCENTYIELD 70%

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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