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

HRID 2267523Notes

Reaction equation

HRID 2267523 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:15]3[C:10](=[C:11]([C:21]([NH2:23])=[O:22])[CH:12]=[C:13]([C:16]4[CH:20]=[CH:19][S:18][CH:17]=4)[CH:14]=3)[NH:9][CH:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:31][CH2:32][CH2:33][S:34](Cl)(=[O:36])=[O:35]>>[Cl:31][CH2:32][CH2:33][S:34]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:15]3[C:10](=[C:11]([C:21]([NH2:23])=[O:22])[CH:12]=[C:13]([C:16]4[CH:20]=[CH:19][S:18][CH:17]=4)[CH:14]=3)[NH:9][CH:8]=2)[CH2:3][CH2:2]1)(=[O:36])=[O:35]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 596006643-(4-piperidinyl)-5-(3-thienyl)-1H-indole-7-carboxamide

Product 1

HCID 687931013-{1-[(2-chloroethyl)sulfonyl]-4-piperidinyl}-5-(3-thienyl)-1H-indole-7-carboxamide

Procedure

3-{1-[(2-chloroethyl)sulfonyl]-4-piperidinyl}-5-(3-thienyl)-1H-indole-7-carboxamide was prepared according to the procedure for intermediate 11. 3-(4-piperidinyl)-5-(3-thienyl)-1H-indole-7-carboxamide (30 mg, 0.09 mmol) was reacted with triethyl amine (0.025 mL, 0.18 mmol) and 2-chloroethylsulfonyl chloride (0.012 mL, 1.08 mmol) to give 3-{1-[(2-chloroethyl)sulfonyl]-4-piperidinyl}-5-(3-thienyl)-1H-indole-7-carboxamide, which was used in the next step without further purification.

Workup

  1. custom3-{1-[(2-chloroethyl)sulfonyl]-4-piperidinyl}-5-(3-thienyl)-1H-indole-7-carboxamide was prepared

Sources & evidence

ORD record
ord-1e9791fac2b74fa38ab7aaf6f1ee02ef
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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