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

HRID 1268742노트

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HRID 1268742 반응식
[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

참가 물질

5

반응물 3

HCID 7672Phenyl isocyanateHCID 516892Sodium BicarbonateHCID 17862984HCID 17862984, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
80 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-fffe74b114e641ea9d32513fce62e24a
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199124B2

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