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

HRID 1776430노트

반응식

HRID 1776430 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-720afc656ec243a5941f741e1c17d91a
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265763B2

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