Triethylamine → HCID 11562628, compound

HRID 656327Notes

Reaction equation

HRID 656327 reaction equation
[O:1]=[C:2]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:4]2([CH2:9][CH2:8][CH:7]([NH:10][C:11]([C@H:13]3[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]3)=[O:12])[CH2:6][CH2:5]2)[O:3]1.[Cl:25][C:26]1[C:27]([CH3:36])=[C:28]([S:32](Cl)(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=1.C(N(CC)CC)C>C(#N)C>[Cl:25][C:26]1[C:27]([CH3:36])=[C:28]([S:32]([N:15]2[CH2:16][CH2:17][CH2:18][C@H:13]([C:11]([NH:10][CH:7]3[CH2:8][CH2:9][C:4]4([C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=5[C:2](=[O:1])[O:3]4)[CH2:5][CH2:6]3)=[O:12])[CH2:14]2)(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5227343-Chloro-2-methylbenzenesulfonyl chlorideHCID 67998363HCID 67998363, compound

Product 1

HCID 11562628HCID 11562628, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (3S)-N-(3-oxo-3H-spiro[2-benzofuran-1,1′-cyclohexan]-4′-yl)piperidine-3carboxamide (11 mg, 0.03 mmol), 3-chloro-2-methylbenzenesulfonyl chloride (6.8 mg, 0.03 mmol), and triethylamine (10.5 μL, 0.075 mmol) in acetonitrile (0.2 mL) was stirred at r.t. for 2 hours. The mixture was purified by flash column to yield 10.2 mg of final product was obtained. Yield: 65%. LCMS: 517.0 (M+H)+; 539.1 (M+Na)+.

Workup

  1. customThe mixture was purified by flash column

Sources & evidence

ORD record
ord-d1182659ce3645848c111ca2574f6afb
Source dataset
uspto-grants-2011_12
Patent number
US08071624B2

Reaction notes

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