Triethylamine → 3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-(2-thienyl)-1H-indole-7-carboxamide

HRID 2267493Notes

Reaction equation

HRID 2267493 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[C:18]([C:29]([NH2:31])=[O:30])[CH:19]=[C:20]([C:23]4[CH:28]=[CH:27][CH:26]=CC=4)[CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:9]1)(=[O:7])=[O:6].N1CCC(C2C3C(=C(C(N)=O)C=C(C4C=C[S:49]C=4)C=3)NC=2)CC1.C(N(CC)CC)C.ClCCCS(Cl)(=O)=O>>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[C:22]3[C:17](=[C:18]([C:29]([NH2:31])=[O:30])[CH:19]=[C:20]([C:23]4[S:49][CH:26]=[CH:27][CH:28]=4)[CH:21]=3)[NH:16][CH:15]=2)[CH2:12][CH2:13]1)(=[O:7])=[O:6]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 590032803-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamideHCID 596006643-(4-piperidinyl)-5-(3-thienyl)-1H-indole-7-carboxamide

Product 1

HCID 590033233-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-(2-thienyl)-1H-indole-7-carboxamideYield 64%

Procedure

The title compound was prepared according to the general procedure for intermediate 11. 3-(4-piperidinyl)-5-(3-thienyl)-1H-indole-7-carboxamide (275 mg, 0.84 mmol) was reacted with triethyl amine (0.35 mL, 2.52 mmol) and 3-chloropropylsulfonyl chloride (0.4 mL, 1.68 mmol) to give the title compound (250 mg, 64%)

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-92f9126e3c254a718472f58fb45c671e
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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