1-Butanol → (RS)-6-(3,5-Bis-trifluoromethyl-benzyl)-4-(3,4-dichloro-benzyl)-3-(2-morpholin-4-yl-ethyl)-7,8-dihydro-6H-1,2,3a,6-tetraaza-azulen-5-one

HRID 1281092노트

반응식

HRID 1281092 반응식
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]1[CH2:13][CH2:12][C:11](=S)[NH:10][CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[C:8]1=[O:24].C(O)CCC.[N:39]1([CH2:45][CH2:46][C:47]([NH:49][NH2:50])=O)[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>>[F:30][C:28]([F:31])([F:29])[C:26]1[CH:25]=[C:5]([CH:4]=[C:3]([C:2]([F:33])([F:32])[F:1])[CH:27]=1)[CH2:6][N:7]1[CH2:13][CH2:12][C:11]2[N:10]([C:47]([CH2:46][CH2:45][N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)=[N:49][N:50]=2)[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[C:8]1=[O:24]

참가 물질

4

반응물 3

HCID 2631-ButanolHCID 16784403-(Morpholin-4-yl)propanehydrazideHCID 11421192(RS)-1-(3,5-bis-trifluoromethyl-benzyl)-3-(3,4-dichloro-benzyl)-5-thioxo-[1,4]diazepan-2-one

생성물 1

HCID 10146213(RS)-6-(3,5-Bis-trifluoromethyl-benzyl)-4-(3,4-dichloro-benzyl)-3-(2-morpholin-4-yl-ethyl)-7,8-dihydro-6H-1,2,3a,6-tetraaza-azulen-5-one수율 59.2%

반응 조건

온도
130 °C

실험 절차

To a solution of 106 mg (0.2 mmol) (RS)-1-(3,5-bis-trifluoromethyl-benzyl)-3-(3,4-dichloro-benzyl)-5-thioxo-[1,4]diazepan-2-one in 1 ml of butan-1-ol 42 mg (0.24 mmol) of 3-morpholin-4-yl-propionic acid hydrazide was added. The reaction mixture was stirred at 130° C. overnight. After evaporation of the solvent in vacuum water (5 ml) was added and the mixture was extracted three times with ethyl acetate. The combined organic layers are dried (MgSO4) and concentrated. The residue was purified by column chromatography (SiO2, dichloromethane/methanol=95:5) to yield 77 mg (59.2%) of the title compound as a light yellow solid. MS m/e (%): 650.0 (M+H+, 100).

후처리

  1. customAfter evaporation of the solvent in vacuum water (5 ml)
  2. additionwas added
  3. extractionthe mixture was extracted three times with ethyl acetate
  4. dry with materialThe combined organic layers are dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (SiO2, dichloromethane/methanol=95:5)

출처 및 근거

ORD 기록
ord-838279cbca694aa3ba4591a7753c8b01
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06452001B2

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