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 498823노트

반응식

HRID 498823 반응식
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]

참가 물질

5

반응물 3

HCID 12249N-MethylisobutylamineHCID 24386Thionyl ChlorideHCID 11212447HCID 11212447, 화합물

생성물 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-one수율 57.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-7b92003a470d4836883aeba9623dbb62
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949542B2

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