1,8-Diazabicyclo(5.4.0)undec-7-ene → 4'-{[4-(1,4-Dioxaspiro[4.5]dec-8-yl)-5-oxo-7-propyl-2-(trifluoromethyl)-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile

HRID 1412491ノート

反応式

HRID 1412491 の反応式
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([NH:11][C:12]3[N:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[NH:14][N:13]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH:36]([C:42](=O)[CH2:43][CH2:44][CH3:45])[C:37](OCC)=[O:38])=[CH:31][CH:30]=1)#[N:22].N12CCCN=C1CCCCC2>C(N(CC)C1C=CC=CC=1)C.C(OCC)(=O)C>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[C:37](=[O:38])[C:36]([CH2:35][C:32]4[CH:33]=[CH:34][C:29]([C:24]5[C:23]([C:21]#[N:22])=[CH:28][CH:27]=[CH:26][CH:25]=5)=[CH:30][CH:31]=4)=[C:42]([CH2:43][CH2:44][CH3:45])[N:13]4[N:14]=[C:15]([C:17]([F:20])([F:18])[F:19])[N:16]=[C:12]34)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10020734Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 67008537N-(1,4-dioxaspiro[4.5]dec-8-yl)-5-(trifluoromethyl)-1H-1,2,4-triazol-3-amine

生成物 1

HCID 670096644'-{[4-(1,4-Dioxaspiro[4.5]dec-8-yl)-5-oxo-7-propyl-2-(trifluoromethyl)-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile収率 41%

試薬・触媒・溶媒 2

HCID 7061N,N-Diethylaniline溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of N-(1,4-dioxaspiro[4.5]dec-8-yl)-5-(trifluoromethyl)-1H-1,2,4-triazol-3-amine (9.87 g), ethyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate (23.59 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (5.05 mL) in N,N-diethylaniline (50 mL) was stirred at 180° C. for 16 hr. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with 1 N hydrochloric acid and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=80/20→60/40 (volume ratio)], and crystallized from diisopropyl ether to give the title compound as a colorless solid (7.91 g, 41%).

後処理

  1. washthe mixture was washed with 1 N hydrochloric acid
  2. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=80/20→60/40 (volume ratio)]
  5. customcrystallized from diisopropyl ether

出典と根拠

ORDレコード
ord-f4ebdcb1ef8e4de896f748cb3640efee
出典データセット
uspto-grants-2014_12
特許番号
US08921379B2

反応ノート

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