Sodium Bicarbonate → N-{2-methyl-4-[1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]-1H-imidazol-1-yl}acetamide

HRID 1907177Notes

Reaction equation

[C:1]([NH:4][NH:5][C:6](=[O:8])[CH3:7])(=[NH:3])[CH3:2].C(=O)(O)[O-].[Na+].Br[CH2:15][C:16]([C:18]1[CH:19]=[N:20][N:21]([CH3:30])[C:22]=1[C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=1)=O>C(#N)C.ClCCl>[CH3:2][C:1]1[N:4]([NH:5][C:6](=[O:8])[CH3:7])[CH:15]=[C:16]([C:18]2[CH:19]=[N:20][N:21]([CH3:30])[C:22]=2[C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)[N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

N′-Ethanimidoylacetohydrazide (147 mg, 1.28 mmol) and sodium bicarbonate (99%, 181 mg, 2.13 mmol) were added to a solution of 2-bromo-1-[1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]ethanone (250 mg, 0.853 mmol) in acetonitrile (9 mL), and the mixture was heated at 80° C. for 3 hours. The reaction was allowed to cool to room temperature, and was then diluted with dichloromethane and filtered through Celite. The filtrate was concentrated in vacuo, and the residue was purified by silica gel chromatography (Eluant: 10% methanol in dichloromethane) to provide the product as a yellow oil. Yield: 236 mg, 0.763 mmol, 89%. LCMS m/z 310.5 (M+1). 1H NMR (400 MHz, CDCl3), presumed to be a mixture of rotamers: δ 2.10 and 1.77 (2 s, 3H), 2.25 and 2.36 (2 s, 3H), 2.44 and 2.46 (2 s, 3H), 3.69 and 3.72 (2 s, 3H), 6.21 (s, 1H), 7.22-7.33 (4H, m, assumed; partially obscured by solvent peak), 7.96 (br s, 1H).

Workup

temperatureto cool to room temperature
filtrationfiltered through Celite
concentrationThe filtrate was concentrated in vacuo
customthe residue was purified by silica gel chromatography (Eluant: 10% methanol in dichloromethane)

Sources & evidence

ORD record: ord-d1dd1ab4ce434f948e11d65714a40b03
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598155B2

Reaction notes

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