1H-Indole-2-carboxamide, 4-(oxiranylmethoxy)- → HCID 21612015, compound

HRID 2107536Notes

Reaction equation

HRID 2107536 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.[CH3:18][O:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:25][CH:24]=1>>[CH3:18][O:19][CH2:20][CH2:21][O:22][C:23]1[CH:24]=[CH:25][C:26]([CH:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:30]2[CH2:31][CH2:32][N:33]([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)[CH2:34][CH2:35]2)=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 41723491H-Indole-2-carboxamide, 4-(oxiranylmethoxy)-HCID 21612014HCID 21612014, compound

Product 1

HCID 21612015HCID 21612015, compound

Procedure

4-(2,3-Epoxypropoxy)-1H-indole-2-carboxamide is reacted with 1-((4-(2-methoxyethoxy)phenyl)phenylmethyl)piperazine to give 4-(3-(4-((4-(2-methoxyethoxy)phenyl)phenylmethyl)piperazin-1-yl)-2-hydroxypropoxy)-1H-indole-2-carboxamide. The compound obtained is reacted with trifluoroacetic anhydride in a mixture of dioxane and pyridine to give 4-(3-(4-((4-(2-methoxyethoxy)phenyl)phenylmethyl)piperazin-1-yl)-2-hydroxypropoxy)-1H-indole-2-carbonitrile.

Sources & evidence

ORD record
ord-d70ff162ce1345ca8f0406f39fd7a8d6
Source dataset
uspto-grants-1990_06
Patent number
US04935414

Reaction notes

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