1,1'-Carbonyldiimidazole → N-Methoxy-N-methyl-1H-indazole-3-carboxamide

HRID 1817507Notes

Reaction equation

HRID 1817507 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=O)=[N:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(C(C)C)CC)(C)C.Cl.[CH3:35][NH:36][O:37][CH3:38]>CN(C=O)C.C(OCC)(=O)C>[CH3:38][O:37][N:36]([CH3:35])[C:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][N:2]=1)=[O:12]

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 78250Indazole-3-carboxylic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531Diisopropylethylamine

Product 1

HCID 16036867N-Methoxy-N-methyl-1H-indazole-3-carboxamideYield 60.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Indazole-3-carboxylic acid (15 g, 0.0925 mol) was dissolved in DMF (40 mL) at room temperature. Carbonyldiimidazole (17 g, 0.104 mol) was added. A solution of diisopropylethylamine (18 mL, 0.104 mol) and N,O-dimethylhydroxylamine HCl (10 g, 0.104 mol) in DMF (10 mL) was added in portions. The reaction was stirred at room temperature overnight. The reaction was taken up in ethyl acetate and washed repeatedly with 2-N HCl, water, and brine. The organic layer was evaporated to a yellow oil, and passed through a pad of silica gel with hexane/ethyl acetate (1:2). The resulting solid was washed with ethyl acetate to give the desired product as a white solid (11.40 g, 0.056 mol).

Workup

  1. washwashed repeatedly with 2-N HCl, water, and brine
  2. customThe organic layer was evaporated to a yellow oil
  3. washThe resulting solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-d2c40725b3cc46fc815c42defac04473
Source dataset
uspto-grants-2009_10
Patent number
US07598286B2

Reaction notes

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