Pyridine → (S)-2-(1-((5-(1-(3-Amino-5-methoxyphenyl)-1H-pyrazol-3-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052645ノート

反応式

HRID 1052645 の反応式
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:14]3[C:13]([NH:15][C@H:16]([C:18]4[N:23]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[C:22](=[O:30])[C:21]5=[C:31]([CH3:34])[CH:32]=[CH:33][N:20]5[N:19]=4)[CH3:17])=[N:12][CH:11]=[N:10][C:9]=3[N:8]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[CH:7]=2)=[N:2]1.[CH3:43][O:44][C:45]1[CH:46]=[C:47]([CH:49]=[C:50](B2OC(C)(C)C(C)(C)O2)[CH:51]=1)[NH2:48].N1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:48][C:47]1[CH:49]=[C:50]([N:1]2[CH:5]=[CH:4][C:3]([C:6]3[C:14]4[C:13]([NH:15][C@H:16]([C:18]5[N:23]([C:24]6[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=6)[C:22](=[O:30])[C:21]6=[C:31]([CH3:34])[CH:32]=[CH:33][N:20]6[N:19]=5)[CH3:17])=[N:12][CH:11]=[N:10][C:9]=4[N:8]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:40])([CH3:42])[CH3:41])[CH:7]=3)=[N:2]2)[CH:51]=[C:45]([O:44][CH3:43])[CH:46]=1

参加物

6

反応物 4

HCID 1049Pyridine2 回HCID 11430Potassium CarbonateHCID 901026273-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamineHCID 178428095HCID 178428095、化合物

生成物 1

HCID 131736246(S)-2-(1-((5-(1-(3-Amino-5-methoxyphenyl)-1H-pyrazol-3-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one収率 14%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

(S)-2-(1-((5-(1H-Pyrazol-3-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (67 mg, 0.12 mmol) was treated with 3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (57 mg, 0.23 mmol), Cu(AcO)2 (32 mg, 0.18 mmol) and pyridine (20 μl, 0.25 mmol) in DMF (1.5 ml). The reaction mixture was submitted at vacuum-argon cycles and stirred at 100° C. under microwave conditions for 2 h. More pyridine and Cu(AcO)2 were added, and the reaction mixture stirred at 100° C. until the reaction was over. The solvent was cooled at room temperature and poured into ice-water, basified with potassium carbonate and extracted with ethyl acetate (×3). The organic phase was successively washed with water and brine, dried over magnesium sulfate, filtered and the solvent evaporated under reduced pressure. The residue (15.3 mg, 14% yield, 75% purity) was used in the next synthetic step without further purification.

後処理

  1. stirringthe reaction mixture stirred at 100° C. until the reaction
  2. temperatureThe solvent was cooled at room temperature
  3. extractionextracted with ethyl acetate (×3)
  4. washThe organic phase was successively washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure
  8. customThe residue (15.3 mg, 14% yield, 75% purity) was used in the next synthetic step without further purification

出典と根拠

ORDレコード
ord-39da8c435435410184be6ca6dd3e9759
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…