Water → 1H-Indazole-4-carboxamide

HRID 1909341Notes

Reaction equation

HRID 1909341 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:16]([OH:18])=O)[C:5]2[CH:6]=[N:7][N:8](C3CCCC3)[C:9]=2[CH:10]=1.C1C[N:22]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.NCC1C(=O)NC(C)=CC=1CO[Si](C(C)(C)C)(C)C.O>CS(C)=O>[NH:8]1[C:9]2[CH:10]=[CH:2][CH:3]=[C:4]([C:16]([NH2:22])=[O:18])[C:5]=2[CH:6]=[N:7]1

Participants

6

Reactant 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

Product 1

HCID 574872701H-Indazole-4-carboxamideYield 115.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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-44-(hydroxymethyl)-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazole-4-carboxamide (1.4 g, 40.9%).

Workup

  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

Sources & evidence

ORD record
ord-a50ebcbdb77c431eafa0ba29cb1196a6
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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