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 639204노트

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HRID 639204 반응식
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]

참가 물질

6

반응물 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

생성물 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-carboxamide수율 87.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

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온도
82 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-68bcd09cb149415fb13c119f9b253843
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691848B2

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