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 2215132ノート

反応式

HRID 2215132 の反応式
[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

参加物

6

反応物 4

HCID 8471Triethylamine2 回HCID 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

生成物 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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2267c93dafbd4fcab5b76a5a1e61ac90
出典データセット
uspto-grants-2006_09
特許番号
US07109193B2

反応ノート

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