2-Phenylpyrrolidine → 5-(5-{[(3S)-3-(dimethylamino)-1-pyrrolidinyl]methyl}-3-thienyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

HRID 1806262Notes

Reaction equation

HRID 1806262 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:38]([NH2:40])=[O:39])[CH:17]=[C:18]([C:21]4[CH:25]=[C:24]([CH2:26][N:27]5[CH2:31][CH2:30][CH2:29][CH:28]5C5C=CC=CC=5)[S:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].C1([CH:47]2CC[CH2:49][NH:48]2)C=CC=CC=1>>[CH3:47][N:48]([CH3:49])[C@H:29]1[CH2:30][CH2:31][N:27]([CH2:26][C:24]2[S:23][CH:22]=[C:21]([C:18]3[CH:19]=[C:20]4[C:15](=[C:16]([C:38]([NH2:40])=[O:39])[CH:17]=3)[NH:14][CH:13]=[C:12]4[CH:9]3[CH2:8][CH2:7][N:6]([S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])[CH2:11][CH2:10]3)[CH:25]=2)[CH2:28]1

Participants

3

Reactant 2

HCID 2618922-PhenylpyrrolidineHCID 16037216HCID 16037216, compound

Product 1

HCID 577326595-(5-{[(3S)-3-(dimethylamino)-1-pyrrolidinyl]methyl}-3-thienyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamideYield 18%

Procedure

The title compound was prepared according to the general procedure for 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-{5-[(2-phenyl-1-pyrrolidinyl)methyl]-3-thienyl}1H-indole-7-carboxamide, substituting (2R)—N,N-dimethyl-2-pyrrolidinamine (114 mg, 1.0 mmol) for 2-phenylpyrrolidine to afford 11 mg of the title compound (18%).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-dca869d87e414e1183e53bd6031e9b69
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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