2(5H)-Furanone → 4-[(3-Chloro-4-fluorophenyl)amino]-6-cyclopentylmethoxy-7-{2-[4-(2-oxo-tetrahydrofuran-4-yl)-piperazin-1-yl]-ethoxy}-quinazoline

HRID 1167171Notes

Reaction equation

HRID 1167171 reaction equation
[O:1]1[CH2:5][CH:4]=[CH:3][C:2]1=[O:6].[Cl:7][C:8]1[CH:9]=[C:10]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([O:33][CH2:34][CH2:35][N:36]4[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]4)=[C:23]([O:26][CH2:27][CH:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)[CH:24]=3)[N:19]=[CH:18][N:17]=2)[CH:11]=[CH:12][C:13]=1[F:14]>CO>[Cl:7][C:8]1[CH:9]=[C:10]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([O:33][CH2:34][CH2:35][N:36]4[CH2:37][CH2:38][N:39]([CH:4]5[CH2:5][O:1][C:2](=[O:6])[CH2:3]5)[CH2:40][CH2:41]4)=[C:23]([O:26][CH2:27][CH:28]4[CH2:29][CH2:30][CH2:31][CH2:32]4)[CH:24]=3)[N:19]=[CH:18][N:17]=2)[CH:11]=[CH:12][C:13]=1[F:14]

Participants

4

Reactant 2

HCID 103412(5H)-Furanone2×HCID 155471684-[(3-Chloro-4-fluorophenyl)amino]-6-cyclopentylmethoxy-7-[2-(piperazin-1-yl)-ethoxy]-quinazoline

Product 1

HCID 101672114-[(3-Chloro-4-fluorophenyl)amino]-6-cyclopentylmethoxy-7-{2-[4-(2-oxo-tetrahydrofuran-4-yl)-piperazin-1-yl]-ethoxy}-quinazoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

46 mg of (5H)-furan-2-one are added to a solution of 230 mg of 4-[(3-chloro-4-fluorophenyl)amino]-6-cyclopentylmethoxy-7-[2-(piperazin-1-yl)-ethoxy]-quinazoline in 2 ml of methanol. The reaction mixture is stirred for 24 hours at ambient temperature, then for another six at 50° C. In total, six more drops of (5H)-furan-2-one are added until the reaction is complete. The solvent is distilled off using the rotary evaporator and the crude product is purified by chromatography over an Alox column (activity stage III) with methylene chloride/methanol (98:2) as eluant. The desired product is obtained as a colourless solid.

Workup

  1. customat 50° C
  2. distillationThe solvent is distilled off
  3. customthe rotary evaporator
  4. customthe crude product is purified by chromatography over an Alox column (activity stage III) with methylene chloride/methanol (98:2) as eluant

Sources & evidence

ORD record
ord-d1917cadd3624a61b5a0a0bc90a13b33
Source dataset
uspto-grants-2003_09
Patent number
US06617329B2

Reaction notes

Loading…