Triethylamine → 3-(4-(6-fluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazol-1-yl)azetidine-1-carboxamide

HRID 2274797Notes

Reaction equation

HRID 2274797 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([N:6]2[CH:10]=[C:9]([C:11]3[C:19]4[C:14](=[CH:15][C:16]([F:20])=[CH:17][CH:18]=4)[N:13]([S:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)(=[O:23])=[O:22])[CH:12]=3)[CH:8]=[N:7]2)[CH2:3]1.CCN(CC)CC.[Si]([N:41]=[C:42]=[O:43])(C)(C)C>>[F:20][C:16]1[CH:15]=[C:14]2[C:19]([C:11]([C:9]3[CH:8]=[N:7][N:6]([CH:4]4[CH2:3][N:2]([C:42]([NH2:41])=[O:43])[CH2:5]4)[CH:10]=3)=[CH:12][N:13]2[S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:22])=[O:23])=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 70696Trimethylsilyl isocyanateHCID 1180602323-(1-(azetidin-3-yl)-1H-pyrazol-4-yl)-6-fluoro-1-(phenylsulfonyl)-1H-indole hydrochloride2×

Product 1

HCID 1180606323-(4-(6-fluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazol-1-yl)azetidine-1-carboxamideYield 100%

Procedure

A mixture of 3-(1-(azetidin-3-yl)-1H-pyrazol-4-yl)-6-fluoro-1-(phenylsulfonyl)-1H-indole hydrochloride (Intermediate 24; 350 mg; 0.81 mmol), Et3N (0.34 ml; 2.44 mmol) and TMSNCO (121 mg; 1.05 mmol) was stirred for 1.5 hours. The reaction mixture was concentrated to afford 355 mg (100%) of the title compound as a brown solid, which was used directly without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-c9ec75e69711414598b150ccf35b9a56
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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