Acetic Anhydride → HCID 67024743, compound

HRID 488424Notes

Reaction equation

HRID 488424 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[Cl:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:43][CH2:44][CH:45]4[CH2:47][CH2:46]4)=[C:24]([NH:27][C:28](=[O:42])[CH:29]=[CH:30][CH2:31][N:32]([CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:33][CH2:34][OH:35])[CH:25]=3)[N:20]=[CH:19][N:18]=2)[CH:12]=[CH:13][C:14]=1[F:15]>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:43][CH2:44][CH:45]4[CH2:47][CH2:46]4)=[C:24]([NH:27][C:28](=[O:42])[CH:29]=[CH:30][CH2:31][N:32]([CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:33][CH2:34][O:35][C:1]([CH3:2])=[O:3])[CH:25]=3)[N:20]=[CH:19][N:18]=2)[CH:12]=[CH:13][C:14]=1[F:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54163752HCID 54163752, compound

Product 1

HCID 67024743HCID 67024743, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

47 μl of acetic anhydride and catalytic amounts of 4-dimethyl-aminopyridine are added to 250 mg of 4-[(3-chloro-4-fluorophenyl)amino]-6-[(4-{N-[(ethoxycarbonyl)methyl]-N-(2-hydroxyethyl)amino}-1-oxo-2-buten-1-yl)amino]-7-cyclopropylmethoxy-quinazoline in 2 ml of methylene chloride. The reaction mixture is stirred overnight at ambient temperatures and then evaporated to dryness. The crude product is purified by chromatography on a silica gel column with methylene chloride, followed by methylene chloride/methanol (9:1) as eluant. Yield: 150 mg (56% of theory), Melting point: 90-92° C. Mass spectrum (ESI+): m/z=614, 616 [M+H]+

Workup

  1. customevaporated to dryness
  2. customThe crude product is purified by chromatography on a silica gel column with methylene chloride

Sources & evidence

ORD record
ord-62abaf3219d4485aa739e382fccf5773
Source dataset
uspto-grants-2005_12
Patent number
US06972288B1

Reaction notes

Loading…