Acetyl chloride → HCID 86690649, compound

HRID 1505617Notes

Reaction equation

HRID 1505617 reaction equation
Cl.[F:2][C:3]1[CH:8]=[C:7]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][C:4]=1[CH2:15][N:16]([CH2:27][C:28]([F:31])([F:30])[F:29])[S:17]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:19])=[O:18].C(N(CC)C(C)C)(C)C.[C:41](Cl)(=[O:43])[CH3:42]>ClCCl>[C:41]([N:12]1[CH2:13][CH2:14][CH:9]([C:7]2[CH:6]=[CH:5][C:4]([CH2:15][N:16]([CH2:27][C:28]([F:31])([F:29])[F:30])[S:17]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:19])=[O:18])=[C:3]([F:2])[CH:8]=2)[CH2:10][CH2:11]1)(=[O:43])[CH3:42]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 86690650HCID 86690650, compound

Product 1

HCID 86690649HCID 86690649, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[[2-fluoro-4-(4-piperidyl)phenyl]methyl]-1-phenyl-N-(2,2,2-trifluoroethyl)methanesulfonamide hydrochloride (100 mg, 0.21 mmol) and N,N-diisopropylethylamine (0.11 mL, 0.62 mmol) in dichloromethane (1.5 mL) was added acetyl chloride (24 mg, 0.31 mmol) and the reaction was stirred at ambient temperature for 2 hours. The reaction was then concentrated and purified by preparative reverse phase HPLC to yield 33.3 mg of N-[4-(1-Acetyl-piperidin-4-yl)-2-fluoro-benzyl]-C-phenyl-N-(2,2,2-trifluoro-ethyl)-methanesulfonamide. 1H NMR (400 MHz, DMSO) δ 7.44-7.38 (m, 5H), 7.38-7.32 (m, 1H), 7.14-7.04 (m, 2H), 4.60 (s, 2H), 4.56-4.47 (m, 1H), 4.41 (s, 2H), 4.07-3.83 (m, 3H), 3.16-3.04 (m, 1H), 2.87-2.74 (m, 1H), 2.63-2.51 (m, 1H), 2.01 (s, 3H), 1.86-1.68 (m, 2H), 1.67-1.49 (m, 1H), 1.49-1.29 (m, 1H). LCMS (m/z) ES+ 487.1 [M+1]+.

Workup

  1. concentrationThe reaction was then concentrated
  2. custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-9e5caef8f6d4400a9ae3eae6e9759d45
Source dataset
uspto-grants-2015_12
Patent number
US09216988B2

Reaction notes

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