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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
US08669265B2

Procedure details

Crude erlotinib hydrochloride (37 gm, obtained in reference example 1), water (370 ml) and chloroform (370 ml) are taken into a reaction flask at 25-30° C. and start stirring. The contents are heated to 5-55° C., sodium hydroxide solution is added at 50-55° C. and then stirred for 15 minutes at 50° C. (clear solution not observed). To the reaction mass added chloroform (200 ml) and methanol (60 ml) and stirred for 15 minutes at 50° C. (clear solution observed). Separated the layers at 50° C., the organic layer is washed with water (200 ml) at 50° C. and then combined the organic layers. To the organic layer added methanol (60 ml) dried over sodium sulfate and distilled the total solvent under vacuum at 50-55° C. To the residue added n-heptane (300 ml) and stirred for 30 minutes at 25-30° C. Filtered the material, washed with n-heptane (70 ml) and then dried the material at 60-65° C. under vacuum for 3 hours 30 minutes to give 34 gm of anhydrous erlotinib free base (HPLC Purity: 98.2%, Moisture Content: 0.2%).
Name
erlotinib hydrochloride
Quantity
37 g
Type
reactant
Reaction Step One
Name
Quantity
370 mL
Type
reactant
Reaction Step One
Quantity
370 mL
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
200 mL
Type
reactant
Reaction Step Three
Quantity
60 mL
Type
solvent
Reaction Step Three
Yield
0.2%

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.O.C(Cl)(Cl)Cl.[OH-].[Na+]>CO>[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] |f:0.1,4.5|

Inputs

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

Conditions

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

Workups

STIRRING
Type
STIRRING
Details
stirred for 15 minutes at 50° C. (clear solution not
Duration
15 min
STIRRING
Type
STIRRING
Details
stirred for 15 minutes at 50° C. (clear solution observed)
Duration
15 min
CUSTOM
Type
CUSTOM
Details
Separated the layers at 50° C.
WASH
Type
WASH
Details
the organic layer is washed with water (200 ml) at 50° C.
ADDITION
Type
ADDITION
Details
To the organic layer added methanol (60 ml)
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
dried over sodium sulfate
DISTILLATION
Type
DISTILLATION
Details
distilled the total solvent under vacuum at 50-55° C
ADDITION
Type
ADDITION
Details
To the residue added n-heptane (300 ml)
STIRRING
Type
STIRRING
Details
stirred for 30 minutes at 25-30° C
Duration
30 min
FILTRATION
Type
FILTRATION
Details
Filtered the material
WASH
Type
WASH
Details
washed with n-heptane (70 ml)
CUSTOM
Type
CUSTOM
Details
dried the material at 60-65° C. under vacuum for 3 hours 30 minutes
Duration
30 min

Outcomes

Product
Name
Type
product
Smiles
COCCOC=1C=C2C(=CC1OCCOC)N=CN=C2NC=3C=CC=C(C3)C#C
Measurements
Type Value Analysis
AMOUNT: MASS 34 g
YIELD: PERCENTYIELD 0.2%
YIELD: CALCULATEDPERCENTYIELD 100.4%

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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