Benzylamine → (S)-N-Benzyl-4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide

HRID 1052717ノート

反応式

HRID 1052717 の反応式
[CH3:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=[O:11])[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7]([C@@H:18]([NH:20][C:21]1[C:22]3[C:29]([C:30](O)=[O:31])=[CH:28][NH:27][C:23]=3[N:24]=[CH:25][N:26]=1)[CH3:19])=[N:6]2.[CH2:33]([NH2:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(N(C(C)C)CC)(C)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CN(C=O)C>[CH2:33]([NH:40][C:30]([C:29]1[C:22]2[C:21]([NH:20][C@H:18]([C:7]3[N:8]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:9](=[O:11])[C:10]4=[C:2]([CH3:1])[CH:3]=[CH:4][N:5]4[N:6]=3)[CH3:19])=[N:26][CH:25]=[N:24][C:23]=2[NH:27][CH:28]=1)=[O:31])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

参加物

6

反応物 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 90102798HCID 90102798、化合物

生成物 1

HCID 73775108(S)-N-Benzyl-4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide収率 46.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

(S)-4-((1-(5-Methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (30 mg, 0.07 mmol), benzylamine (20 mg, 0.19 mmol) and diisopropylethylamine (50 μl, 0.29 mmol) were dissolved in DMF (1.5 ml) and stirred for 30 min. The reaction flask was then sealed and T3P® (50% in DMF, 50 μl) was added dropwise and the reaction mixture was stirred overnight at room temperature. The mixture was poured into ice-water and extracted with ethyl acetate. The resulting organic solution was washed with water and brine, dried over magnesium sulphate, filtered and the solvents were removed under reduced pressure. The product was purified by flash chromatography (0% to 5% DCM/MeOH) to give 17 mg (46% yield) of the title compound as a white solid.

後処理

  1. customThe reaction flask was then sealed
  2. stirringthe reaction mixture was stirred overnight at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe resulting organic solution was washed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure
  8. customThe product was purified by flash chromatography (0% to 5% DCM/MeOH)

出典と根拠

ORDレコード
ord-08684804f58646e590a41fc0c12a6bfe
出典データセット
uspto-grants-2016_07
特許番号
US09388189B2

反応ノート

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