Potassio isocyanate → (S)-1-(3-(4-Amino-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)-5-methoxyphenyl)urea

HRID 1052843노트

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HRID 1052843 반응식
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1[C:28]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[C:30]([NH2:36])[CH:29]=1.[N-:37]=[C:38]=[O:39].[K+]>O.C(O)(=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]([C:28]2[CH:29]=[C:30]([NH:36][C:38]([NH2:37])=[O:39])[CH:31]=[C:32]([O:34][CH3:35])[CH:33]=2)=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[N:5]=[CH:6][N:7]=1

참가 물질

6

반응물 2

HCID 11051572Potassio isocyanateHCID 118433902(S)-2-(1-((6-Amino-5-(3-amino-5-methoxyphenyl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

생성물 1

HCID 90102996(S)-1-(3-(4-Amino-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)-5-methoxyphenyl)urea수율 57.1%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매2회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

(S)-2-(1-((6-Amino-5-(3-amino-5-methoxyphenyl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (87 mg, 0.18 mmol) was suspended in a mixture of water (1.5 ml) and acetic acid (1.5 ml) and cooled in an ice bath to 0° C. This mixture was treated with a solution of potassium isocyanate (29 mg, 0.36 mmol) in water (0.5 ml). The reaction mixture was stirred at 0° C. for 1 h and then led to warm to room temperature. The crude was diluted with ethyl acetate and washed with saturated ammonium chloride solution and brine. After evaporation of the solvent, the residue was purified by flash chromatography (50 to 100%, hexane-ethyl acetate) using SP1® Purification System to give 54 mg (57% yield) of the title compound as a solid. Purity 99%.

후처리

  1. temperatureto warm to room temperature
  2. washwashed with saturated ammonium chloride solution and brine
  3. customAfter evaporation of the solvent
  4. customthe residue was purified by flash chromatography (50 to 100%, hexane-ethyl acetate)
  5. customSP1® Purification System

출처 및 근거

ORD 기록
ord-42be8d9b461842939f9a4dffd1d30d8f
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388189B2

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