Water → 6-bromo-1-cyclopentyl-N-((4-(hydroxymethyl)-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazole-4-carboxamide

HRID 1501712노트

반응식

HRID 1501712 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:16]([OH:18])=O)[C:5]2[CH:6]=[N:7][N:8]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[C:9]=2[CH:10]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:52][CH2:53][C:54]1[C:55](=[O:70])[NH:56][C:57]([CH3:69])=[CH:58][C:59]=1[CH2:60][O:61][Si](C(C)(C)C)(C)C.O>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:16]([NH:52][CH2:53][C:54]2[C:55](=[O:70])[NH:56][C:57]([CH3:69])=[CH:58][C:59]=2[CH2:60][OH:61])=[O:18])[C:5]2[CH:6]=[N:7][N:8]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[C:9]=2[CH:10]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 2724699PyBOPHCID 674684486-bromo-1-cyclopentyl-1H-indazole-4-carboxylic acidHCID 682947603-(aminomethyl)-4-(((tert-butyldimethylsilyl)oxy)methyl)-6-methylpyridin-2(1H)-one

생성물 1

HCID 682948306-bromo-1-cyclopentyl-N-((4-(hydroxymethyl)-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazole-4-carboxamide수율 40.9%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a solution of 6-bromo-1-cyclopentyl-1H-indazole-4-carboxylic acid (2.3 g, 7.5 mmol) in DMSO (30 mL), PyBOP (5.82 g, 11.20 mmol) was added and reaction stirred at room temperature for 15 min. 3-(Aminomethyl)-4-(((tert-butyldimethylsilyl)oxy)methyl)-6-methylpyridin-2(1H)-one (2.52 g, 8.96 mmol) was then added and reaction mixture stirred overnight. On completion, water was added and the resulting precipitate filtered and washed with water. This solid was then stirred with acetonitrile for 10 min and filtered again to obtain 6-bromo-1-cyclopentyl-N-((4-(hydroxymethyl)-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazole-4-carboxamide (1.4 g, 40.9%).

후처리

  1. customreaction
  2. customreaction mixture
  3. stirringstirred overnight
  4. filtrationthe resulting precipitate filtered
  5. washwashed with water
  6. stirringThis solid was then stirred with acetonitrile for 10 min
  7. filtrationfiltered again

출처 및 근거

ORD 기록
ord-ce0f51ee63814fd294daf3665ab1f766
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206157B2

반응 노트

불러오는 중…