Dimethylformamide → 1-ethyl-N-methoxy-N-methyl-1H-pyrazole-5-carboxamide

HRID 2234664Notes

Reaction equation

HRID 2234664 reaction equation
C([N:4]([CH:7]([CH3:9])[CH3:8])[CH2:5][CH3:6])(C)C.Cl.[CH3:11][NH:12][O:13][CH3:14].F[P-](F)(F)(F)(F)F.[N:22]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)[C:26]2C=CC=CC=2N=N1.CN(C)C=[O:51]>>[CH3:14][O:13][N:12]([CH3:11])[C:9]([C:7]1[N:4]([CH2:5][CH3:6])[N:22]=[CH:26][CH:8]=1)=[O:51]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2724699PyBOP

Product 1

HCID 577316551-ethyl-N-methoxy-N-methyl-1H-pyrazole-5-carboxamide

Procedure

A solution of 2-ethyl-2H-pyrazole-3-carboxylic, di-iso-propylethylamine, and N,O-dimethylhydroxylamine hydrochloride in N,N-dimethylformamide was stirred at 0° C. (Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate was added and the reaction mixture was slowly warmed to room temperature. The reaction was stirred for 18 hours. The mixture was concentrated, and 20% 2-propanol in dichloromethane added. The mixture was washed with a saturated aqueous solution of sodium bicarbonate, dried over sodium sulfate, and concentrated. The crude material was purified by flash chromatography to give 2-ethyl-2H-pyrazole-3-carboxylic acid methoxy-methyl-amide. 1H NMR (250 MHz, CDCl3) δ 7.47 (d, J=2 Hz, 1H), 6.71 (d, J=2 Hz, 1H), 4.48 (quart, J=7.3 Hz, 2H), 3.62 (s, 3H), 3.34 (s, 3H), 1.42 (t, J=7.0 Hz, 3H).

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated
  3. addition20% 2-propanol in dichloromethane added
  4. washThe mixture was washed with a saturated aqueous solution of sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-ff3c8090ae8a46dd849ec4f2cebc02ba
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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