4-Chloro-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline → 1-(4-Chloro-3-trifluoromethylphenyl)-3-(2-{6-methoxy-7-[3-(4-methylpiperazin-1-yl)-propoxy]quinazolin-4-ylamino}benzothiazol-6-yl)urea
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:25][C:26]1[S:27][C:28]2[CH:34]=[C:33]([NH:35][C:36]([NH:38][C:39]3[CH:44]=[CH:43][C:42]([Cl:45])=[C:41]([C:46]([F:49])([F:48])[F:47])[CH:40]=3)=[O:37])[CH:32]=[CH:31][C:29]=2[N:30]=1>>[Cl:45][C:42]1[CH:43]=[CH:44][C:39]([NH:38][C:36]([NH:35][C:33]2[CH:32]=[CH:31][C:29]3[N:30]=[C:26]([NH:25][C:2]4[C:11]5[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]6[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]6)=[C:9]([O:12][CH3:13])[CH:10]=5)[N:5]=[CH:4][N:3]=4)[S:27][C:28]=3[CH:34]=2)=[O:37])=[CH:40][C:41]=1[C:46]([F:48])([F:47])[F:49]Participants
3
Reactant 2
Product 1
Procedure
1-(4-Chloro-3-trifluoromethylphenyl)-3-(2-{6-methoxy-7-[3-(4-methylpiperazin-1-yl)-propoxy]quinazolin-4-ylamino}benzothiazol-6-yl)urea was prepared from 4-chloro-6-methoxy-7-[3-(4-methylpiperazin-1-yl)-propoxy]quinazoline (Intermediate 6, 38.6 mg, 0.11 mmol) and 1-(2-aminobenzothiazol-6-yl)-3-(4-chloro-3-tri-fluoromethylphenyl)urea (Intermediate 3, 42.5 mg, 0.11 mmol) according to GP 1. The crude product was isolated by centrifugation and washed thoroughly with dioxane, methanol, water, and finally methanol. After drying, tetrahydrofuran was added (0.5 mL) and the mixture was filtered through glass wool to obtain pure product (pale yellow solid, 36 mg, 52 μmol, 47%). LC/ESI-MS: m/z=701 [M(35Cl)+H]+; m/z=699 [M(35Cl)−H]−; Rt=2.88 min.