Diisopropylethylamine → Phenyl 4-(4-acetylpiperazin-1-yl)-2-fluorobenzyl(cyclobutyl)sulfamate

HRID 1403724노트

반응식

HRID 1403724 반응식
[O-]S(C(F)(F)F)(=O)=O.C[N+]1C=CN([S:15]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:17])=[O:16])C=1.[CH:25]1([NH:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([N:37]3[CH2:42][CH2:41][N:40]([C:43](=[O:45])[CH3:44])[CH2:39][CH2:38]3)=[CH:33][C:32]=2[F:46])[CH2:28][CH2:27][CH2:26]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:43]([N:40]1[CH2:39][CH2:38][N:37]([C:34]2[CH:35]=[CH:36][C:31]([CH2:30][N:29]([CH:25]3[CH2:26][CH2:27][CH2:28]3)[S:15](=[O:17])(=[O:16])[O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:32]([F:46])[CH:33]=2)[CH2:42][CH2:41]1)(=[O:45])[CH3:44]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 866906371-(4-(4-((Cyclobutylamino)methyl)-3-fluorophenyl)piperazin-1-yl)ethanoneHCID 904096313-Methyl-1-(phenoxysulfonyl)-1H-imidazol-3-ium triflate

생성물 1

HCID 78210216Phenyl 4-(4-acetylpiperazin-1-yl)-2-fluorobenzyl(cyclobutyl)sulfamate수율 29.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-methyl-1-(phenoxysulfonyl)-1H-imidazol-3-ium triflate (143 mg, 0.6 mmol) and 1-(4-(4-((cyclobutylamino)methyl)-3-fluorophenyl)piperazin-1-yl)ethanone (150 mg, 0.49 mmol) in DCM (20 mL) was added diisopropylethylamine (1 mL). The mixture was stirred at ambient temperature for 16 h. After the solvent was removed, the residue was purified by prep-HPLC to provide the title compound (67.3 mg, 29.6%). 1H NMR (400 MHz, DMSO-d6) δ 7.44-7.40 (m, 2 H), 7.34-7.24 (m, 4 H), 6.79-6.67 (m, 2 H), 4.46 (s, 2 H), 4.20-4.17 (m, 1 H), 3.73-3.66 (m, 4 H), 3.26-3.17 (m, 4 H), 2.19-2.15 (m, 2 H), 2.14 (s, 3 H), 2.03-1.98 (m, 2 H), 1.62-1.52 (m, 2 H). LCMS (ESI): m/z 483.9 [M+Na+].

후처리

  1. customAfter the solvent was removed
  2. customthe residue was purified by prep-HPLC

출처 및 근거

ORD 기록
ord-62839011bfdf4d03971f10d18f092aed
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912219B2

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