Methanol → Erlotinib

HRID 1846130Notes

Reaction equation

HRID 1846130 reaction equation
[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]

Participants

5

Reactant 3

HCID 887MethanolHCID 10340Sodium CarbonateHCID 176871Erlotinib Hydrochloride

Product 1

HCID 176870Erlotinib

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
27.5 °C

Procedure

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.

Workup

  1. customto obtain a suspension
  2. stirringstirred for one hour at 25-30° C
  3. stirringstirred for one hour
  4. customThe crude erlotinib base was isolated by filtration and suck
  5. customdried
  6. additionbefore adding it to 250 ml (5 vol.) of water at 25-30° C.
  7. stirringstirred for 30 min

Sources & evidence

ORD record
ord-563c454a17e84a4aab00778962aacdb9
Source dataset
uspto-grants-2015_02
Patent number
US08952022B2

Reaction notes

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