Diisopropylethylamine → N-[4-(4-Acetylpiperazin-1-yl)-2-fluorobenzyl]-3,5-dichloro-N-cyclobutyl-benzenesulfonamide

HRID 1505602Notes

Reaction equation

HRID 1505602 reaction equation
[CH:1]1([NH:5][CH2:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:18][CH2:17][N:16]([C:19](=[O:21])[CH3:20])[CH2:15][CH2:14]3)=[CH:9][C:8]=2[F:22])[CH2:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[Cl:32][C:33]1[CH:34]=[C:35]([S:40](Cl)(=[O:42])=[O:41])[CH:36]=[C:37]([Cl:39])[CH:38]=1>ClCCl>[C:19]([N:16]1[CH2:15][CH2:14][N:13]([C:10]2[CH:11]=[CH:12][C:7]([CH2:6][N:5]([CH:1]3[CH2:2][CH2:3][CH2:4]3)[S:40]([C:35]3[CH:34]=[C:33]([Cl:32])[CH:38]=[C:37]([Cl:39])[CH:36]=3)(=[O:42])=[O:41])=[C:8]([F:22])[CH:9]=2)[CH2:18][CH2:17]1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5223883,5-Dichlorobenzenesulfonyl chlorideHCID 866906371-(4-(4-((Cyclobutylamino)methyl)-3-fluorophenyl)piperazin-1-yl)ethanone

Product 1

HCID 71612422N-[4-(4-Acetylpiperazin-1-yl)-2-fluorobenzyl]-3,5-dichloro-N-cyclobutyl-benzenesulfonamideYield 44.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-(4-((cyclobutylamino)methyl)-3-fluorophenyl)piperazin-1-yl)ethanone (55 mg, 0.18 mmol) in dichloromethane (1 mL) was added N,N-diisopropylethylamine (0.047 mL, 0.27 mmol), followed by 3,5-dichlorobenzene-1-sulfonyl chloride (50 mg, 0.20 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 41 mg of N-(4-(4-acetylpiperazin-1-yl)-2-fluorobenzyl)-3,5-dichloro-N-cyclobutylbenzenesulfonamide. 1H NMR (400 MHz, DMSO) δ 7.95 (t, J=1.8 Hz, 1H), 7.72 (d, J=1.8 Hz, 2H), 7.18 (t, J=8.9 Hz, 1H), 6.80-6.74 (m, 1H), 6.74-6.67 (m, 1H), 4.40 (s, 2H), 4.35-4.20 (m, 1H), 3.62-3.51 (m, 4H), 3.25-3.17 (m, 2H), 3.16-3.10 (m, 2H), 2.04 (s, 3H), 2.02-1.88 (m, 4H), 1.55-1.48 (m, 2H); LCMS (m/z) ES+ 514.0 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-72f9d775f50d4f29b28e4369e5280bd3
Source dataset
uspto-grants-2015_12
Patent number
US09216988B2

Reaction notes

Loading…