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molecular formula C22H23N3O4 B000232 Erlotinib CAS No. 183321-74-6

Erlotinib

Cat. No. B000232
M. Wt: 393.4 g/mol
InChI Key: AAKJLRGGTJKAMG-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US09340515B2

Procedure details

The wet cake of crude erlotinib hydrochloride was added to 500 ml (10 vol.) of methanol under stirring at 25-30° C. to obtain a suspension. Sodium carbonate (33.8 g, 0.3197 mol) was added to the mixture at 25-30° C. and stirred for one hour at 25-30° C. 500 ml (10 vol.) of water was added to the reaction mixture and stirred for one hour. The crude erlotinib base was isolated by filtration and suck dried before adding it to 250 ml (5 vol.) of water at 25-30° C. and stirred for 30 min. The erlotinib base was isolated by filtration and washed with 50 ml (1 vol.) of water and suck dried to get 70 g as a wet cake. This wet cake was dried under reduced pressure at 100 mm Hg for 3 hour at 60-65° C. to afford 63 g of erlotinib base as an off-white powder.
Name
erlotinib hydrochloride
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
500 mL
Type
reactant
Reaction Step One
Quantity
33.8 g
Type
reactant
Reaction Step Two
Name
Quantity
500 mL
Type
solvent
Reaction Step Three

Identifiers

REACTION_CXSMILES
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:20]([NH:21][C:22]3[CH:23]=[CH:24][CH:25]=[C:26]([C:28]#[CH:29])[CH:27]=3)=[N:19][CH:18]=[N:17][C:9]2=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][O:15][CH3:16].Cl.CO.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:20]([NH:21][C:22]3[CH:27]=[C:26]([C:28]#[CH:29])[CH:25]=[CH:24][CH:23]=3)=[N:19][CH:18]=[N:17][C:9]2=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][O:15][CH3:16] |f:0.1,3.4.5|

Inputs

Step One
Name
erlotinib hydrochloride
Quantity
0 (± 1) mol
Type
reactant
Smiles
COCCOC=1C=C2C(=CC1OCCOC)N=CN=C2NC=3C=CC=C(C3)C#C.Cl
Name
Quantity
500 mL
Type
reactant
Smiles
CO
Step Two
Name
Quantity
33.8 g
Type
reactant
Smiles
C([O-])([O-])=O.[Na+].[Na+]
Step Three
Name
Quantity
500 mL
Type
solvent
Smiles
O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
27.5 (± 2.5) °C
Stirring
Type
CUSTOM
Details
under stirring at 25-30° C.
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
to obtain a suspension
STIRRING
Type
STIRRING
Details
stirred for one hour at 25-30° C
Duration
1 h
STIRRING
Type
STIRRING
Details
stirred for one hour
Duration
1 h
CUSTOM
Type
CUSTOM
Details
The crude erlotinib base was isolated by filtration and suck
CUSTOM
Type
CUSTOM
Details
dried
ADDITION
Type
ADDITION
Details
before adding it to 250 ml (5 vol.) of water at 25-30° C.
STIRRING
Type
STIRRING
Details
stirred for 30 min
Duration
30 min

Outcomes

Product
Name
Type
product
Smiles
COCCOC1=C(C=C2C(=C1)C(=NC=N2)NC3=CC=CC(=C3)C#C)OCCOC

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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