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

HRID 1854159ノート

反応式

HRID 1854159 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-4f345ed09aba4a6ab4107a3c588990a1
出典データセット
uspto-grants-2015_02
特許番号
US08962620B2

反応ノート

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