Pyridine → (S)-2-(1-((5-(1-(3-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 1052625ノート

反応式

HRID 1052625 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](B(O)O)[CH:48]=[CH:49][CH:50]=1.N1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:43][O:44][C:45]1[CH:50]=[C:49]([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:48]=[CH:47][CH:46]=1

参加物

7

反応物 4

HCID 1049PyridineHCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 178428095HCID 178428095、化合物

生成物 1

HCID 131736240(S)-2-(1-((5-(1-(3-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 9%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
75 °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 (88 mg, 0.15 mmol) was dissolved in N,N-dimethylformamide (1.5 ml). (3-Methoxyphenyl)boronic acid (46 mg, 0.30 mmol), copper(II) acetate (4 mg, 0.02 mmol) and pyridine (28 μL, 0.34 mmol) were added and the mixture was stirred at 75° C. during 96 h. The reaction was poured into ice-water mixture, basified to pH 10 with sodium carbonate and extracted twice with ethyl acetate. The organics were combined and washed with water, brine, dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified using SP1® Purification System (0% to 50%, hexane-ethyl acetate) to give 9 mg (9% yield) of the title compound.

後処理

  1. extractionextracted twice with ethyl acetate
  2. washwashed with water, brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified
  7. customSP1® Purification System (0% to 50%, hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-255ecc6891f24aa4808bc10f2d2c983d
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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