1,2-Dichloroethane → HCID 47149234, compound

HRID 216330Notes

Reaction equation

HRID 216330 reaction equation
[CH3:1][NH:2][O:3][CH3:4].[N:5]1([C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][N:11]=2)[CH:9]=[CH:8][CH:7]=[N:6]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl>[CH3:4][O:3][N:2]([CH3:1])[C:14](=[O:16])[C:13]1[CH:17]=[CH:18][C:10]([N:5]2[CH:9]=[CH:8][CH:7]=[N:6]2)=[N:11][CH:12]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 14232N,O-DimethylhydroxylamineHCID 757711-HydroxybenzotriazoleHCID 27636146-(1H-pyrazol-1-yl)nicotinic acid

Product 1

HCID 47149234HCID 47149234, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,O-Dimethylhydroxylamine (1.03 g, 10.6 mmol) was added to an ambient temperature solution of 6-(1H-pyrazol-1-yl)nicotinic acid (2 g, 10.6 mmol), EDC (2.4 g, 12.7 mmol), HOBt (1.94 g, 12.7 mmol) and NMM (5.2 mL, 47.6 mmol) in methylene chloride (100 mL). After stirring at ambient temperature overnight, the reaction mixture was diluted with methylene chloride and washed successively with saturated aqueous sodium bicarbonate and brine, dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% ethyl acetate/hexane afforded N-methoxy-N-methyl-6-(1H-pyrazol-1-yl)nicotinamide.

Workup

  1. washwashed successively with saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2750ff61d60b45698c90dddaa4e38ddc
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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