N-(4-Bromophenethyl)acetamide → 5-(4-{2-[(cyclohexylcarbonyl)amino]ethyl}phenyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

HRID 1806304Notes

Reaction equation

HRID 1806304 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[C:15]3[C:19](=[C:20]([C:22]([NH2:24])=[O:23])[CH:21]=2)[NH:18][CH:17]=[C:16]3[CH:25]2[CH2:30][CH2:29][N:28]([S:31]([CH2:34][CH3:35])(=[O:33])=[O:32])[CH2:27][CH2:26]2)=[CH:9][CH:8]=1)(=[O:3])[CH3:2].Br[C:37]1[CH:42]=[CH:41]C(CCNC(=O)C)=[CH:39][CH:38]=1>>[CH:2]1([C:1]([NH:4][CH2:5][CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:14]=[C:15]4[C:19](=[C:20]([C:22]([NH2:24])=[O:23])[CH:21]=3)[NH:18][CH:17]=[C:16]4[CH:25]3[CH2:30][CH2:29][N:28]([S:31]([CH2:34][CH3:35])(=[O:32])=[O:33])[CH2:27][CH2:26]3)=[CH:9][CH:8]=2)=[O:3])[CH2:41][CH2:42][CH2:37][CH2:38][CH2:39]1

Participants

3

Reactant 2

HCID 16097949N-(4-Bromophenethyl)acetamideHCID 667229205-{4-[2-(acetylamino)ethyl]phenyl}-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

Product 1

HCID 577327595-(4-{2-[(cyclohexylcarbonyl)amino]ethyl}phenyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamideYield 52.5%

Procedure

The title compound was prepared according to the general procedure of 5-{4-[2-(acetylamino)ethyl]phenyl}-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide, substituting N-[2-(4-bromophenyl)ethyl]cyclohexanecarboxamide (100 mg, 0.324 mmol) for N-[2-(4-bromophenyl)ethyl]acetamide. Purified by flash chromatography to afford 32 mg of the title compound (52.5%).

Workup

  1. customThe title compound was prepared
  2. customPurified by flash chromatography

Sources & evidence

ORD record
ord-200db19a3c3c453a998e0dfb79558be2
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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