Triethylamine → 1-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-3-[2-methyl-4-(6-methyl-3,4-dihydro-2H-quinoline-1-carbonyl)-phenyl]-propan-1-one

HRID 220894ノート

反応式

HRID 220894 の反応式
[CH3:1][C:2]([CH3:26])([CH3:25])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11](=[O:24])[CH2:12][CH2:13][C:14]2[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][C:15]=2[CH3:23])[CH2:7][CH2:6]1.C(N(CC)CC)C.[CH3:34][C:35]1[CH:36]=[C:37]2[C:42](=[CH:43][CH:44]=1)[NH:41][CH2:40][CH2:39][CH2:38]2>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][C:2]([CH3:26])([CH3:25])[CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([C:11](=[O:24])[CH2:12][CH2:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([N:41]3[C:42]4[C:37](=[CH:36][C:35]([CH3:34])=[CH:44][CH:43]=4)[CH2:38][CH2:39][CH2:40]3)=[O:19])=[CH:16][C:15]=2[CH3:23])[CH2:9][CH2:10]1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 666786-Methyl-1,2,3,4-tetrahydroquinolineHCID 575552774-{3-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-3-oxo-propyl}-3-methyl-benzoic Acid

生成物 1

HCID 575553611-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-3-[2-methyl-4-(6-methyl-3,4-dihydro-2H-quinoline-1-carbonyl)-phenyl]-propan-1-one収率 6%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

DMAP (51 mg, 0.42 mmol) and WSCD (161 mg, 0.84 mmol) were added to a solution of 4-{3-[4-(3,3-dimethyl-butyl)-piperazin-1-yl]-3-oxo-propyl}-3-methyl-benzoic acid from Example E44 (150 mg, 0.42 mmol) in dichloromethane (10 ml) and triethylamine (0.176 ml, 1.26 mmol) and the mixture was stirred for 30 min at room temperature. 6-Methyl-1,2,3,4-tetrahydro-quinoline (67 mg, 0.46 mmol) was added and the mixture was stirred for 20 h at room temperature then solvents were removed in vacuo. The residue was redissolved in EtOAC, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo. The residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloromethane) to give a white solid identified as the title compound (12 mg, 6%).

後処理

  1. customsolvents were removed in vacuo
  2. dissolutionThe residue was redissolved in EtOAC
  3. washwashed with saturated NaHCO3
  4. dry with materialbrine, dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloromethane)
  7. customto give a white solid

出典と根拠

ORDレコード
ord-507054cd9dd44cf99cac82d3144d3ac4
出典データセット
uspto-grants-2012_06
特許番号
US08202858B2

反応ノート

読み込み中…