Potassium Carbonate → 4-({2-[1-(2-fluorobenzyl)-1H-indazol-3-yl]-5-hydroxypyrimidin-4-yl}amino)pyridine-3-carbonitrile

HRID 1776430ノート

反応式

HRID 1776430 の反応式
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[N:19]=[C:18]([NH2:20])[C:17]([O:21]C)=[CH:16][N:15]=2)=[N:6]1.C(=O)([O-])[O-].[K+].[K+].Br[C:34]1[CH:39]=[CH:38][N:37]=[CH:36][C:35]=1[C:40]#[N:41]>CN(C)C=O>[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[N:19]=[C:18]([NH:20][C:34]3[CH:39]=[CH:38][N:37]=[CH:36][C:35]=3[C:40]#[N:41])[C:17]([OH:21])=[CH:16][N:15]=2)=[N:6]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 223295224-Bromopyridine-3-carbonitrileHCID 867324252-[1-(2-fluorobenzyl)-1H-indazol-3-yl]-5-methoxypyrimidin-4-amine

生成物 1

HCID 1363414254-({2-[1-(2-fluorobenzyl)-1H-indazol-3-yl]-5-hydroxypyrimidin-4-yl}amino)pyridine-3-carbonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

50 mg of 4-amino-2-[1-(2-fluorobenzyl)-1H-indazol-3-yl]pyrimidin-5-ol (1-11-1, 0.149 mmol, 1. eq.) were dissolved in 3 ml of N,N-dimethylformamide. 103 mg of potassium carbonate (0.746 mmol, 5 eq.) and 32.8 mg of 4-bromopyridine-3-carbonitrile (0.179 mmol, 1.2 eq.) were added. The reaction mixture was stirred at 100° C. bath temperature for 18 hours. After cooling at room temperature the mixture was filtered off and washed with dichloromethane. The filtrate was concentrated in vacuo. The residue was purified by preparative HPLC and preparative TLC to yield 4.21 mg (0.01 mmol, 6.1%) of the analytically pure target compound.

後処理

  1. temperatureAfter cooling at room temperature the mixture
  2. filtrationwas filtered off
  3. washwashed with dichloromethane
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was purified by preparative HPLC and preparative TLC
  6. customto yield 4.21 mg (0.01 mmol, 6.1%) of the analytically pure target compound

出典と根拠

ORDレコード
ord-720afc656ec243a5941f741e1c17d91a
出典データセット
uspto-grants-2016_02
特許番号
US09265763B2

反応ノート

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