2-Hydroxy-N,N-dimethyl-2-{5-[3-(2-methyl-2H-pyrazol-3-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamide → 2-hydroxy-N,N-dimethyl-2-{5-[3-(2-methyl-2H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamide

HRID 886630노트

반응식

HRID 886630 반응식
[OH:1][CH:2]([C:8]1[CH:9]=[N:10][CH:11]=[C:12]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[N:24]([CH3:28])[N:25]=[CH:26][CH:27]=4)=[CH:21][N:20](COCC[Si](C)(C)C)[C:17]3=[N:18][CH:19]=2)[CH:13]=1)[C:3]([N:5]([CH3:7])[CH3:6])=[O:4]>ClCCl.FC(F)(F)C([O-])=O>[OH:1][CH:2]([C:8]1[CH:9]=[N:10][CH:11]=[C:12]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[N:24]([CH3:28])[N:25]=[CH:26][CH:27]=4)=[CH:21][NH:20][C:17]3=[N:18][CH:19]=2)[CH:13]=1)[C:3]([N:5]([CH3:7])[CH3:6])=[O:4]

참가 물질

3

반응물 1

HCID 598250742-Hydroxy-N,N-dimethyl-2-{5-[3-(2-methyl-2H-pyrazol-3-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamide

생성물 1

HCID 1360142832-hydroxy-N,N-dimethyl-2-{5-[3-(2-methyl-2H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamide수율 87.7%

시약·촉매·용매 1

HCID 22481192Dichloromethane trifluoroacetate용매

실험 절차

2-Hydroxy-N,N-dimethyl-2-{5-[3-(2-methyl-2H-pyrazol-3-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamide (71 mg, 0.1 mmol) was stirred in dichloromethane/trifluoroacetate acid (1 ml/1 ml) at room temperature for 2 hours. The solvents were removed under vacuum and the crude material was stirred in dichloromethane/ethylenediamine (1 ml/1 ml) for 2 hours at room temperature. The solvents were removed in vacuo and the residue was dissolved in DMSO, filtered and purified by reverse phase HPLC and lyophilized to afford 2-hydroxy-N,N-dimethyl-2-{5-[3-(2-methyl-2H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamide (33 mg, 61% yield). 1H NMR (500 MHz, DMSO-d6) δ 2.87 (s, 3H), 3.00 (s, 3H), 3.93 (s, 3H), 7.53 (m, 1H), 7.94 (s, 1H), 8.12 (m, 1H), 8.25 (m, 1H), 8.56 (m, 1H), 8.65 (m, 1H), 8.92 (m, 1H), 12.38 (s, 1H). MS: m/z 377.2 (M+H+).

후처리

  1. customThe solvents were removed under vacuum
  2. customThe solvents were removed in vacuo
  3. dissolutionthe residue was dissolved in DMSO
  4. filtrationfiltered
  5. custompurified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-9adf80b716f24e9782c19c2652d15ee3
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242280B2

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