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

HRID 2267542Notes

Reaction equation

HRID 2267542 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=2)[NH:13][CH:12]=[C:11]3[CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:33][CH2:34][CH2:35][CH2:36][S:37](Cl)(=[O:39])=[O:38]>>[Cl:33][CH2:34][CH2:35][CH2:36][S:37]([N:23]1[CH2:24][CH2:25][CH:20]([C:11]2[C:10]3[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[CH:9]=3)[NH:13][CH:12]=2)[CH2:21][CH2:22]1)(=[O:39])=[O:38]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 59600665HCID 59600665, compound

Product 1

HCID 687913173-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-(4-fluorophenyl)-1H-indole-7-carboxamide

Procedure

3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-(4-fluorophenyl)-1H-indole-7-carboxamide was prepared according to the procedure for intermediate 11. 5-(4-fluorophenyl)-3-(4-piperidinyl)-1H-indole-7-carboxamide (20 mg, 0.059 mmol) was reacted with triethyl amine (0.03 mL, 0.236 mmol) and 3-chloropropylsulfonyl chloride (0.03 mL, 0.118 mmol) to give 3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-(4-fluorophenyl)-1H-indole-7-carboxamide, which was used in the next step without further purification.

Workup

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

Sources & evidence

ORD record
ord-be11c2759d914cf893cd00d324ccfdfe
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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