1H-Indole-2-carboxamide, 4-(oxiranylmethoxy)- → 4-(3-(4-((4-Difluoromethoxyphenyl)phenylmethyl)piperazin-1-yl)-2-hydroxypropoxy)-1H-indole-2-carboxamide

HRID 2107527Notes

Reaction equation

[O:1]1[CH2:17][CH:2]1[CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[C:8]([C:14]([NH2:16])=[O:15])[NH:9]2.[F:18][CH:19]([F:40])[O:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:23][CH:22]=1>CO>[F:40][CH:19]([F:18])[O:20][C:21]1[CH:22]=[CH:23][C:24]([CH:27]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:28]2[CH2:33][CH2:32][N:31]([CH2:17][CH:2]([OH:1])[CH2:3][O:4][C:5]3[CH:13]=[CH:12][CH:11]=[C:10]4[C:6]=3[CH:7]=[C:8]([C:14]([NH2:16])=[O:15])[NH:9]4)[CH2:30][CH2:29]2)=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3.45 g of 4-(2,3-epoxypropoxy)-1H-indole-2-carboxamide and 4.70 g of 1-((4-difluoromethoxyphenyl)phenylmethyl)piperazine are dissolved at 40° C. in 75 ml of methanol. The mixture is then concentrated to dryness in vacuo, the syrupy residue is heated at 80° C. for 15 minutes and, after cooling, the solidified product is triturated with hexane and filtered off with suction.

Workup

concentrationThe mixture is then concentrated to dryness in vacuo
temperatureafter cooling
customthe solidified product is triturated with hexane
filtrationfiltered off with suction

Sources & evidence

ORD record: ord-4eeb185a4b654d12a8024821accc6077
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04935414

Reaction notes

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