Sodium hydride → HCID 89463179, compound

HRID 1473277Notes

Reaction equation

HRID 1473277 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][N:5]([CH3:26])[C:6]([C:8]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:11]=[CH:10][C:9]=1[C:22](OC)=[O:23])=[O:7].[H-].[Na+].[NH4+].[Cl-].O>CN(C=O)C>[OH:23][C:22]1[C:9]2[CH:10]=[N:11][N:12]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:8]=2[C:6](=[O:7])[N:5]([CH3:26])[C:4]=1[C:3]([O:2][CH3:1])=[O:27]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 57429219Ammonium chloride monohydrateHCID 89463160HCID 89463160, compound

Product 1

HCID 89463179HCID 89463179, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 5-((2-methoxy-2-oxoethyl)(methyl)carbamoyl)-1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylate (1.1 g, 2.93 mmol) in DMF (20 mL) was added NaH (0.12 g, 2.85 mmol, 60% in mineral oil) and the mixture was stirred a ambient temperature under nitrogen atmosphere for 50 min. Saturated NH4Cl/water was slowly added and stirring at ambient temperature continued for 50 min. The solid was filtered, dissolved in dichloromethane and the filtrate dried over sodium sulfate and concentrated to provide the title compound (0.60 g, 60%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.2 (s, 1H), 8.1 (s 1H), 7.22 (d, 2H), 6.9 (d, 2H), 5.8 (s, 2H), 3.9 (s, 3H), 3.7 (s, 3H), 3.42 (s, 3H); ES-LCMS: 344 (M+1).

Workup

  1. stirringstirring at ambient temperature
  2. waitcontinued for 50 min
  3. filtrationThe solid was filtered
  4. dissolutiondissolved in dichloromethane
  5. dry with materialthe filtrate dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1779b92d55934e1f9b09bf8a284edfb8
Source dataset
uspto-grants-2015_04
Patent number
US09012642B2

Reaction notes

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