Erlotinib
货号 B000232
分子量: 393.4 g/mol
InChI 键: AAKJLRGGTJKAMG-UHFFFAOYSA-N
注意: 仅供研究使用。不适用于人类或兽医用途。
Patent
US08669265B2
Procedure details
Crude erlotinib hydrochloride (100 gm, obtained in reference example 1), water (400 ml) and ethyl acetate (1600 ml) are taken into a reaction flask at 25-30° C. and start stirring. The contents are heated to 60° C., pH of the mass is adjusted to 9 to 10 by adding sodium hydroxide solution (30-40 ml) at 60-65° C. and then stirred for 30-35 minutes at 60-65° C. Separated the layers at 60-65° C., the organic layer is dried with sodium sulfate and then distilled off the solvent completely under vacuum at 50° C. The residue is cooled to 25-30° C., n-heptane (800 ml) is added and the stirred for 45 minutes to 1 hour at 25-30° C. Filtered the compound, washed with n-heptane (200 ml) and then dried at 60-65° C. to give 90 gm of anhydrous erlotinib free base (HPLC Purity: 99.1%, Moisture Content: 0.1%).
Name
erlotinib hydrochloride
Quantity
100 g
Type
reactant
Reaction Step One
Name
Yield
0.1%
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.[OH-].[Na+]>C(OCC)(=O)C>[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:0.1,3.4|
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Inputs
Step One
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Name
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erlotinib hydrochloride
|
|
Quantity
|
100 g
|
|
Type
|
reactant
|
|
Smiles
|
COCCOC=1C=C2C(=CC1OCCOC)N=CN=C2NC=3C=CC=C(C3)C#C.Cl
|
|
Name
|
|
|
Quantity
|
400 mL
|
|
Type
|
reactant
|
|
Smiles
|
O
|
|
Name
|
|
|
Quantity
|
1600 mL
|
|
Type
|
solvent
|
|
Smiles
|
C(C)(=O)OCC
|
Step Two
|
Name
|
|
|
Quantity
|
35 (± 5) mL
|
|
Type
|
reactant
|
|
Smiles
|
[OH-].[Na+]
|
Conditions
Temperature
|
Control Type
|
UNSPECIFIED
|
|
Setpoint
|
60 °C
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
start stirring
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
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Workups
STIRRING
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Type
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STIRRING
|
|
Details
|
stirred for 30-35 minutes at 60-65° C
|
|
Duration
|
32.5 (± 2.5) min
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
Separated the layers at 60-65° C.
|
DRY_WITH_MATERIAL
|
Type
|
DRY_WITH_MATERIAL
|
|
Details
|
the organic layer is dried with sodium sulfate
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DISTILLATION
|
Type
|
DISTILLATION
|
|
Details
|
distilled off the solvent completely under vacuum at 50° C
|
TEMPERATURE
|
Type
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TEMPERATURE
|
|
Details
|
The residue is cooled to 25-30° C.
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
n-heptane (800 ml) is added
|
STIRRING
|
Type
|
STIRRING
|
|
Details
|
the stirred for 45 minutes to 1 hour at 25-30° C
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
Filtered the compound
|
WASH
|
Type
|
WASH
|
|
Details
|
washed with n-heptane (200 ml)
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
dried at 60-65° C.
|
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 | 90 g | |
| YIELD: PERCENTYIELD | 0.1% | |
| YIELD: CALCULATEDPERCENTYIELD | 98.3% |
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. |
