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

HRID 1806261Notes

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]5[C:32]5C=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].[C:41]1([CH:47]2[CH2:51][CH2:50][CH2:49][NH:48]2)C=CC=CC=1>>[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]5[CH2:32][N:48]5[CH2:41][CH2:47][CH2:51][CH2:50][CH2:49]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]

Participants

Reactant 2

HCID 2618922-Phenylpyrrolidine

HCID 16037216HCID 16037216, compound

Product 1

HCID 160372173-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-{[2-(1-piperidinylmethyl)-1-pyrrolidinyl]methyl}-3-thienyl)-1H-indole-7-carboxamideYield 32%

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 1-(2-pyrrolidinylmethyl)piperidine (168.3 mg, 1.0 mmol) for 2-phenylpyrrolidine to afford 21 mg of the title compound (32%).

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-6286c9d1f3e64668ae97e0e3aef117df
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354406B2

Reaction notes

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