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 1052843ノート

反応式

HRID 1052843 の反応式
[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

参加物

6

反応物 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

生成物 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)urea収率 57.1%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

(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%.

後処理

  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

出典と根拠

ORDレコード
ord-42be8d9b461842939f9a4dffd1d30d8f
出典データセット
uspto-grants-2016_07
特許番号
US09388189B2

反応ノート

読み込み中…