Dimethyl Sulfoxide → N-[2-(Dimethylamino)-2-phenylethyl]-10-[(2'-methoxy-1,1'-biphenyl-4-YL)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-C][1,4]benzodiazepine-3-carboxamide

HRID 639204ノート

反応式

HRID 639204 の反応式
ClC(Cl)(Cl)[C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH3:34])=[CH:23][CH:22]=3)=[O:20])[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4].[NH2:37][CH2:38][CH:39]([N:46]([CH3:48])[CH3:47])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.CS(C)=O.C(N(CC)CC)C>C(#N)C>[CH3:47][N:46]([CH3:48])[CH:39]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:38][NH:37][C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH3:34])=[CH:23][CH:22]=3)=[O:20])[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 241652(2-Amino-1-phenylethyl)dimethylamineHCID 160384072,2,2-trichloro-1-{10-[(2'-methoxy-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone

生成物 1

HCID 16038408N-[2-(Dimethylamino)-2-phenylethyl]-10-[(2'-methoxy-1,1'-biphenyl-4-YL)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-C][1,4]benzodiazepine-3-carboxamide収率 87.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
82 °C

実験手順

To a suspension of 2,2,2-trichloro-1-{10-[(2′-methoxy-1,1′-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone of Example 1 (1.21 g, 2.25 mmole) in acetonitrile (25 mL) was added a solution of (2-amino-1-phenylethyl) dimethylamine (0.250 g, 1.52 mmole) in acetonitrile (5 mL), followed by dimethylsulfoxide (5 equivalents) and triethylamine (2.2 equivalents). The mixture was stirred at 82° C. under nitrogen for 18 hours. The solvent was evaporated, and the residue diluted with dichloromethane. The solution was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was flash chromatographed over silica gel Merck-60 using a gradient of 30 to 80% ethyl acetate in dichloromethane to provide the title compound as a light brown amorphous solid (0.777 g). MS [(+)ESI, m/z]: 585.19 [M+H]+ Anal. Calcd for C37H36N4O3.0.2 C4H8O2: C, 75.38; H, 6.29; N, 9.30. Found: C, 75.42; H, 6.38; N, 9.04.

後処理

  1. customThe solvent was evaporated
  2. additionthe residue diluted with dichloromethane
  3. washThe solution was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customchromatographed over silica gel Merck-60

出典と根拠

ORDレコード
ord-68bcd09cb149415fb13c119f9b253843
出典データセット
uspto-grants-2010_04
特許番号
US07691848B2

反応ノート

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