Cesium fluoride → (S)-4-Amino-N-(3-methoxy-5-(methylsulfonamido)phenyl)-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidine-5-carboxamide

HRID 1052851ノート

反応式

HRID 1052851 の反応式
[NH2:1][C@H:2]([C:4]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8](=[O:16])[C:7]2=[C:17]([CH3:20])[CH:18]=[CH:19][N:6]2[N:5]=1)[CH3:3].[NH2:21][C:22]1[C:27]([C:28]([NH:30][C:31]2[CH:36]=[C:35]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH:34]=[C:33]([O:42][CH3:43])[CH:32]=2)=[O:29])=[C:26](Cl)[N:25]=[CH:24][N:23]=1.CCN(C(C)C)C(C)C.[F-].[Cs+]>C(O)(C)(C)C>[NH2:21][C:22]1[C:27]([C:28]([NH:30][C:31]2[CH:36]=[C:35]([NH:37][S:38]([CH3:41])(=[O:39])=[O:40])[CH:34]=[C:33]([O:42][CH3:43])[CH:32]=2)=[O:29])=[C:26]([NH:1][C@H:2]([C:4]2[N:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:8](=[O:16])[C:7]3=[C:17]([CH3:20])[CH:18]=[CH:19][N:6]3[N:5]=2)[CH3:3])[N:25]=[CH:24][N:23]=1

参加物

6

反応物 4

HCID 25953Cesium fluorideHCID 81531DiisopropylethylamineHCID 90102580(S)-2-(1-Aminoethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneHCID 90103324HCID 90103324、化合物

生成物 1

HCID 90102993(S)-4-Amino-N-(3-methoxy-5-(methylsulfonamido)phenyl)-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidine-5-carboxamide収率 23%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

反応条件

温度
80 °C

実験手順

(S)-2-(1-Aminoethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (117 mg, 0.38 mmol), 4-amino-6-chloro-N-(3-methoxy-5-(methylsulfonamido)phenyl)pyrimidine-5-carboxamide (266 mg, 65% purity, 0.46 mmol), DIEA (404 μl, 2.32 mmol) and cesium fluoride (175 mg, 1.14 mmol) were suspended in tert-butanol (12 ml) and the mixture was heated at 80° C. in a sealed tube for 3 days. The solvent was evaporated under reduced pressure and the reaction mixture was diluted with ethyl acetate and washed with saturated ammonium chloride solution and brine. After evaporation of the solvent, the residue was purified by reverse phase using SP1® Purification System to give 54 mg (23% yield) as a solid. Purity 97%.

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe reaction mixture was diluted with ethyl acetate
  3. washwashed with saturated ammonium chloride solution and brine
  4. customAfter evaporation of the solvent
  5. customthe residue was purified by reverse phase
  6. custom® Purification System
  7. customto give 54 mg (23% yield) as a solid

出典と根拠

ORDレコード
ord-ff5b7d35709d4a719a6edf5149050e82
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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