Hydrochloric Acid → Erlotinib Hydrochloride

HRID 238994Notes

Reaction equation

HRID 238994 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[C:9]([O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:22][C:23]1[CH:24]=[C:25]([C:29]#[CH:30])[CH:26]=[CH:27][CH:28]=1.Cl>O>[CH3:16][O:15][CH2:14][CH2:13][O:12][C:9]1[CH:10]=[C:11]2[C:2]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[CH:30])[CH:24]=3)=[N:3][CH:4]=[N:5][C:6]2=[CH:7][C:8]=1[O:17][CH2:18][CH2:19][O:20][CH3:21].[ClH:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 104682Benzenamine, 3-ethynyl-HCID 112899424-Chloro-6,7-bis(2-methoxyethoxy)quinazoline

Product 1

HCID 176871Erlotinib HydrochlorideYield 84.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.0 g of 4-chloro-6,7-bis(2-methoxyethoxy) quinazoline was suspended in 75 ml of water and 2.55 g of 3-aminophenyl acetylene was added at 25-30° C. followed by 1.0 ml of 50% hydrochloric acid. The reaction mass was heated at 35- 40° C. for 1 hour. The solid obtained was filtered and washed with water. The product was dried at 40-45° C. to obtain 5.8 g of erlotinib hydrochloride.

Workup

  1. temperatureThe reaction mass was heated at 35- 40° C. for 1 hour
  2. customThe solid obtained
  3. filtrationwas filtered
  4. washwashed with water
  5. customThe product was dried at 40-45° C.

Sources & evidence

ORD record
ord-822db084f00c47e49c48714e4525ecda
Source dataset
uspto-grants-2014_02
Patent number
US08642758B2

Reaction notes

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