N-Methylisobutylamine → 4-(3-{2-[(Isobutyl-methyl-amino)-methyl]-pyridin-4-yl}-phenyl)-7-methyl-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 498823ノート

反応式

HRID 498823 の反応式
O[CH2:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:10]=[C:11]([C:15]3[CH2:21][C:20](=[O:22])[NH:19][C:18]4[CH:23]=[C:24]([C:28]([F:31])([F:30])[F:29])[C:25]([CH3:27])=[CH:26][C:17]=4[N:16]=3)[CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][N:4]=1.S(Cl)(Cl)=O.[CH2:36]([NH:40][CH3:41])[CH:37]([CH3:39])[CH3:38]>C(Cl)Cl>[CH2:36]([N:40]([CH2:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:10]=[C:11]([C:15]3[CH2:21][C:20](=[O:22])[NH:19][C:18]4[CH:23]=[C:24]([C:28]([F:31])([F:30])[F:29])[C:25]([CH3:27])=[CH:26][C:17]=4[N:16]=3)[CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][N:4]=1)[CH3:41])[CH:37]([CH3:39])[CH3:38]

参加物

5

反応物 3

HCID 12249N-MethylisobutylamineHCID 24386Thionyl ChlorideHCID 11212447HCID 11212447、化合物

生成物 1

HCID 223171384-(3-{2-[(Isobutyl-methyl-amino)-methyl]-pyridin-4-yl}-phenyl)-7-methyl-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one収率 57.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A stirred suspension of 4-[3-(2-hydroxymethyl-pyridin-4-yl)-phenyl]-7-methyl-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example 283) (213 mg, 0.50 mmol) and thionyl chloride (0.11 ml, 1.50 mmol) in CH2Cl2 was refluxed for 45 min, evaporated to dryness and dissolved in DMF (3 ml). To the stirred solution N-isobutyl-methyl-amine (436 mg, 5.0 mmol) was added and the reaction mixture was stirred at RT for 1 h. Aqueous work-up (CH2Cl2) and further purification by column chromatography on silica gel (CH2Cl2/MeOH 15:1) yielded the title compound as a light yellow solid (142 mg, 57%).

後処理

  1. temperaturewas refluxed for 45 min
  2. customevaporated to dryness
  3. dissolutiondissolved in DMF (3 ml)
  4. customAqueous work-up (CH2Cl2) and further purification by column chromatography on silica gel (CH2Cl2/MeOH 15:1)

出典と根拠

ORDレコード
ord-7b92003a470d4836883aeba9623dbb62
出典データセット
uspto-grants-2005_09
特許番号
US06949542B2

反応ノート

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