Hydrochloric Acid → Erlotinib hydrochloride

HRID 523965

Reaction equation

HRID 523965 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]2[C:12]([NH:16][C:17]3[CH:22]=[C:21]([C:23]#[CH:24])[CH:20]=[CH:19][CH:18]=3)=[N:13][CH:14]=[N:15][C:9]2=[CH:8][C:7]=1[O:25][CH2:26][CH2:27][O:28][CH3:29].[ClH:30]>C(O)CCCC>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]2[C:12]([NH:16][C:17]3[CH:18]=[CH:19][CH:20]=[C:21]([C:23]#[CH:24])[CH:22]=3)=[N:13][CH:14]=[N:15][C:9]2=[CH:8][C:7]=1[O:25][CH2:26][CH2:27][O:28][CH3:29].[ClH:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 176870Erlotinib

Product 1

HCID 176871Erlotinib hydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Conditions

Temperature
7.5 °C

Procedure

115 g (0.292 mol) of erlotinib base was added to 2300 ml (20 vol) of 1-pentanol at 25-30° C. The mixture was cooled to 5 to 10° C. and stirred for 30 min. to obtain a suspension. 57.5 g of aqueous hydrochloric acid at a concentration of 35% (w/w) was added drop wise at 5-10° C. and the mixture stirred for 1 hour. The product was isolated by filtration and washed with 230 ml (2 vol.) of 1-pentanol. The product was dried under reduced pressure (50 mm Hg) at 0-60° C. to obtain 113 g of erlotinib hydrochloride polymorph A as a white solid.

Workup

  1. customto obtain a suspension
  2. stirringthe mixture stirred for 1 hour
  3. customThe product was isolated by filtration
  4. washwashed with 230 ml (2 vol.) of 1-pentanol
  5. customThe product was dried under reduced pressure (50 mm Hg) at 0-60° C.

Sources & evidence

ORD record
ord-d2aa1b856f7a4a12be5b88ef642f98af
Source dataset
uspto-grants-2016_05
Patent number
US09340515B2

Linked notes

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