Phenylmethanesulfonyl chloride → HCID 86690658, compound

HRID 1505627Notes

Reaction equation

HRID 1505627 reaction equation
Cl.[O:2]1[C:8]2[CH:9]=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([C:19](=[O:21])[CH3:20])[CH2:15][CH2:14]3)[CH:11]=[CH:12][C:7]=2[CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)C(C)C)(C)C.[C:31]1([CH2:37][S:38](Cl)(=[O:40])=[O:39])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>ClCCl>[C:31]1([CH2:37][S:38]([N:5]2[CH2:6][C:7]3[CH:12]=[CH:11][C:10]([N:13]4[CH2:14][CH2:15][N:16]([C:19](=[O:21])[CH3:20])[CH2:17][CH2:18]4)=[CH:9][C:8]=3[O:2][CH2:3][CH2:4]2)(=[O:40])=[O:39])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 74740Phenylmethanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86690659HCID 86690659, compound

Product 1

HCID 86690658HCID 86690658, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-(2,3,4,5-tetrahydrobenzo[f][1,4]oxazepin-8-yl)piperazin-1-yl)ethanone hydrochloride (80 mg, 0.26 mmol) and N,N-diisopropylethylamine (0.17 mL, 0.94 mmol) in dichloromethane (1.5 mL) was added phenylmethanesulfonyl chloride (76 mg, 0.39 mmol) and the reaction was stirred at ambient temperature for 16 hours. The reaction was then concentrated and purified by preparative reverse phase HPLC to yield 61 mg of 1-[4-(4-phenylmethanesulfonyl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepin-8-yl)-piperazin-1-yl]-ethanone. 1H NMR (400 MHz, DMSO) δ 7.38-7.27 (m, 5H), 7.03 (d, J=8.3 Hz, 1H), 6.63-6.58 (m, 1H), 6.58-6.55 (m, 1H), 4.36 (s, 2H), 4.22 (s, 2H), 3.96-3.90 (m, 2H), 3.59-3.51 (m, 4H), 3.51-3.46 (m, 2H), 3.18-3.12 (m, 2H), 3.12-3.04 (m, 2H), 2.02 (s, 3H); LCMS (m/z) ES+ 430.1 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-05e1b10fa7594045849ff3de65ee6212
Source dataset
uspto-grants-2015_12
Patent number
US09216988B2

Reaction notes

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