Phenyl isocyanate → N-{5-[2-(Cyclopentylamino)pyridin-4-yl]-4-(3-methylphenyl)-1,3-thiazol-2-yl}-N'-phenylurea

HRID 1268742ノート

反応式

HRID 1268742 の反応式
[CH:1]1([NH:6][C:7]2[CH:12]=[C:11]([C:13]3[S:17][C:16]([NH2:18])=[N:15][C:14]=3[C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=3)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:26]1([N:32]=[C:33]=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])O.[Na+]>CN(C)C(=O)C>[CH:1]1([NH:6][C:7]2[CH:12]=[C:11]([C:13]3[S:17][C:16]([NH:18][C:33]([NH:32][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:34])=[N:15][C:14]=3[C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=3)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 7672Phenyl isocyanateHCID 516892Sodium BicarbonateHCID 17862984HCID 17862984、化合物

生成物 1

HCID 18446692N-{5-[2-(Cyclopentylamino)pyridin-4-yl]-4-(3-methylphenyl)-1,3-thiazol-2-yl}-N'-phenylurea収率 40.8%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of [5-(2-cyclopentylamino-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amine (0.43 g, 1.2 mmol) in N,N-dimethylacetamide (10 mL) was added phenyl isocyanate (0.19 mL, 1.8 mmol) and the mixture was stirred at 80° C. for 1 hr. Into the reaction mixture was poured aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=1:1). The obtained crude crystals were recrystallized from ethyl acetate to give the title compound (0.23 g, yield 39%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=1:1)
  6. customThe obtained crude crystals
  7. customwere recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-fffe74b114e641ea9d32513fce62e24a
出典データセット
uspto-grants-2007_04
特許番号
US07199124B2

反応ノート

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