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

HRID 1403724ノート

反応式

HRID 1403724 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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+].

後処理

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

出典と根拠

ORDレコード
ord-62839011bfdf4d03971f10d18f092aed
出典データセット
uspto-grants-2014_12
特許番号
US08912219B2

反応ノート

読み込み中…