Benzenesulfonyl chloride → HCID 178523804, compound

HRID 656333Notes

Reaction equation

HRID 656333 reaction equation
Cl.Cl.[N:3]1[CH:8]=[CH:7][C:6]([O:9][C@H:10]2[CH2:15][CH2:14][C@H:13]([NH:16][C:17]([C@H:19]3[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]3)=[O:18])[CH2:12][CH2:11]2)=[CH:5][CH:4]=1.[C:25]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>C(#N)C>[C:25]1([S:31]([N:21]2[CH2:22][CH2:23][CH2:24][C@H:19]([C:17]([NH:16][C@H:13]3[CH2:12][CH2:11][C@H:10]([O:9][C:6]4[CH:5]=[CH:4][N:3]=[CH:8][CH:7]=4)[CH2:15][CH2:14]3)=[O:18])[CH2:20]2)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 178478893HCID 178478893, compound

Product 1

HCID 178523804HCID 178523804, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (3S)-N-[trans-4-(pyridin-4-yloxy)cyclohexyl]piperidine-3-carboxamide dihydrochloride (28 mg, purity: 40%, 0.03 mmol), benzenesulfonyl chloride (6.3 mg, 0.036 mmol), triethylamine (16 μL, 0.12 mmol) in acetonitrile (1 mL) was stirred at r.t. overnight. the mixture was purified with prep. HPLC. 5.9 mg (45%) of final product was obtained. LCMS: m/z 444.1 (M+H)+; 466.1 (M+Na)+.

Workup

  1. customthe mixture was purified with prep

Sources & evidence

ORD record
ord-a07e2f2fde0b4aea867f9370dc7ec493
Source dataset
uspto-grants-2011_12
Patent number
US08071624B2

Reaction notes

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