Cyclobutanone → 4-[5-(4-Cyclobutyl-[1,4]diazepane-1-carbonyl)-1H-indole-2-carbonyl]-piperazine-1-carboxylic acid ethyl ester

HRID 1992498Notes

Reaction equation

C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][C:21]([C:26]([N:28]2[CH2:33][CH2:32][N:31]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:30][CH2:29]2)=[O:27])=[CH:20]3)=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.[C:39]1(=O)[CH2:42][CH2:41][CH2:40]1>>[CH2:37]([O:36][C:34]([N:31]1[CH2:30][CH2:29][N:28]([C:26]([C:21]2[NH:22][C:23]3[C:19]([CH:20]=2)=[CH:18][C:17]([C:15]([N:11]2[CH2:12][CH2:13][CH2:14][N:8]([CH:39]4[CH2:42][CH2:41][CH2:40]4)[CH2:9][CH2:10]2)=[O:16])=[CH:25][CH:24]=3)=[O:27])[CH2:33][CH2:32]1)=[O:35])[CH3:38]

Participants

Reactant 2

HCID 14496Cyclobutanone

HCID 685365464-[2-(4-ethoxycarbonyl-piperazine-1-carbonyl)-1H-indole-5-carbonyl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 685358214-[5-(4-Cyclobutyl-[1,4]diazepane-1-carbonyl)-1H-indole-2-carbonyl]-piperazine-1-carboxylic acid ethyl ester

Procedure

The title compound was synthesized in analogy to example 47, from 4-[2-(4-ethoxycarbonyl-piperazine-1-carbonyl)-1H-indole-5-carbonyl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester and cyclobutanone. Light-yellow solid. MS (m/z): 482.4 (M+H)+.

Sources & evidence

ORD record: ord-1a9c31cc3e69481ba822866e32081f38
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07648979B2

Reaction notes

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