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

HRID 2107527
Notes
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Reaction equation

HRID 2107527 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 41723491H-Indole-2-carboxamide, 4-(oxiranylmethoxy)-HCID 14405370HCID 14405370, compound

Product 1

HCID 144053714-(3-(4-((4-Difluoromethoxyphenyl)phenylmethyl)piperazin-1-yl)-2-hydroxypropoxy)-1H-indole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. concentrationThe mixture is then concentrated to dryness in vacuo
  2. temperatureafter cooling
  3. customthe solidified product is triturated with hexane
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes