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 1281092ノート

反応式

HRID 1281092 の反応式
[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]

参加物

4

反応物 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

生成物 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-one収率 59.2%

反応条件

温度
130 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-838279cbca694aa3ba4591a7753c8b01
出典データセット
uspto-grants-2002_09
特許番号
US06452001B2

反応ノート

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