Triethylamine → 7,8-Dimethoxy-10-{[2-methyl-2'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl]carbonyl}-[(10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl)carbonyl]-4-piperidinone

HRID 2215132노트

반응식

HRID 2215132 반응식
[CH3:1][O:2][C:3]1[C:4]([O:36][CH3:37])=[CH:5][C:6]2[N:12]([C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]([F:30])([F:29])[F:28])=[C:17]([CH3:31])[CH:16]=3)=[O:14])[CH2:11][C:10]3=[CH:32][CH:33]=[CH:34][N:9]3[CH2:8][C:7]=2[CH:35]=1.[O:38]=[C:39](Cl)OC(Cl)(Cl)Cl.C(N(CC)CC)C.[NH:53]1[CH2:58][CH2:57][C:56](=[O:59])[CH2:55][CH2:54]1>ClCCl>[CH3:1][O:2][C:3]1[C:4]([O:36][CH3:37])=[CH:5][C:6]2[N:12]([C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]([F:30])([F:29])[F:28])=[C:17]([CH3:31])[CH:16]=3)=[O:14])[CH2:11][C:10]3=[CH:32][CH:33]=[C:34]([C:39]([N:53]4[CH2:58][CH2:57][C:56](=[O:59])[CH2:55][CH2:54]4)=[O:38])[N:9]3[CH2:8][C:7]=2[CH:35]=1

참가 물질

6

반응물 4

HCID 8471Triethylamine2회HCID 10426DiphosgeneHCID 337214-PiperidoneHCID 219477487,8-Dimethoxy-[10,11-dihydro-5H-pyrrolo [2,1-c][1,4]benzodiazepin-10-yl][2-methyl-2'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]methanone

생성물 1

HCID 101459497,8-Dimethoxy-10-{[2-methyl-2'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl]carbonyl}-[(10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl)carbonyl]-4-piperidinone

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of the 7,8-dimethoxy-[10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl][2-methyl-2′-trifluoromethyl-[1,1′-biphenyl]-4-yl]methanone of Example 12, Step D (0.31 mmol), diphosgene (1.1 equiv.) and triethylamine (1.5 equiv.) in dichloromethane (5 mL) was stirred at room temperature overnight. The solvent was removed in vacuo, the residue was dissolved in dichloromethane (5 mL), and then triethylamine (1.5 equiv.) and 4-piperidone (1.5 equiv.) were added. The reaction mixture was stirred overnight, washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. The residue was first chromatographed on silica gel eluting with 2% methanol in dichloromethane and then chromatographed again with 2% methanol in ethyl acetate to provide the title compound as a yellow solid, m.p. 132–134° C.

후처리

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane (5 mL)
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was first chromatographed on silica gel eluting with 2% methanol in dichloromethane
  8. customchromatographed again with 2% methanol in ethyl acetate

출처 및 근거

ORD 기록
ord-2267c93dafbd4fcab5b76a5a1e61ac90
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109193B2

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