1,2-Dichloroethane → N-methoxy-N-methyl-1H-indazole-5-carboxamide

HRID 1752544Notes

Reaction equation

HRID 1752544 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[CH3:13][NH:14][O:15][CH3:16].C(N(CC)CC)C.C(Cl)CCl>ClCCl.CN(C)C=O>[CH3:16][O:15][N:14]([CH3:13])[C:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][N:2]=[CH:3]2)=[O:12]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 42484541H-Indazole-5-carboxylic acid

Product 1

HCID 62814299N-methoxy-N-methyl-1H-indazole-5-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of Example 75A (1.6 g, 10 mmol) and N,O-dimethylhydroxylamine (1.1 g, 11 mmol) in dichloromethane (40 mL) and dimethylformamide (10 mL) was added triethylamine (1.67 mL, 12 mmol) and EDC (2.1 g, 11 mmol), and the mixture was stirred at room temperature for 24 hours. The solvents were evaporated under reduced pressure, and the resulting residue was diluted with ethyl acetate and washed with water. The organic layer was dried over sodium sulfate and purified by silica gel column chromatography in ethyl acetate to afford the title compound. MS (ESI+) m/z 206.0 (M+H)+.

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. additionthe resulting residue was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. custompurified by silica gel column chromatography in ethyl acetate

Sources & evidence

ORD record
ord-2e5d65556ea249fa8a6984cd39a7a461
Source dataset
uspto-grants-2015_10
Patent number
US09163007B2

Reaction notes

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