Chloroform methanol → HCID 178424524, compound

HRID 1508139Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[NH:14][CH:15]=[C:16]([C:18]#[N:19])[N:17]=2)=[O:12])=[C:6]([C:20]2[CH2:25][CH2:24][C:23]([CH3:27])([CH3:26])[CH2:22][CH:21]=2)[CH:5]=1)(=[O:3])[CH3:2].C[Mg+].[Br-].CO.[CH:33](Cl)(Cl)Cl>C1COCC1>[CH3:26][C:23]1([CH3:27])[CH2:24][CH2:25][C:20]([C:6]2[CH:5]=[C:4]([C:1]([OH:3])([CH3:33])[CH3:2])[CH:9]=[CH:8][C:7]=2[NH:10][C:11]([C:13]2[NH:14][CH:15]=[C:16]([C:18]#[N:19])[N:17]=2)=[O:12])=[CH:21][CH2:22]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a slurry of 4-cyano-1H-imidazole-2-carboxylic acid [4-acetyl-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (6.00 g, 0.0160 mol) in 100 mL of THF at −78° C. was added a solution of MeMgBr (3.0 M in THF, 22 mL, 0.066 mol) via syringe over a 20-min period. The reaction was allowed to warm to ca. 0° C. over a 30-min period at which point there was no starting material evident by thin layer chromatography (10% MeOH—CHCl3). The reaction was cooled to −78° C., quenched by the addition of saturated aqueous NH4Cl (100 mL) and allowed to warm to 0° C. The mixture was extracted with ether (2×150 mL) and dried (Na2SO4). The solvent was concentrated to afford the title compound as a white solid (6.40 g, 100%). The NMR and mass spectral data were identical to those for the compound produced in Example 14, step (d).

Workup

temperatureThe reaction was cooled to −78° C.
customquenched by the addition of saturated aqueous NH4Cl (100 mL)
temperatureto warm to 0° C
extractionThe mixture was extracted with ether (2×150 mL)
dry with materialdried (Na2SO4)
concentrationThe solvent was concentrated

Sources & evidence

ORD record: ord-9cb6df9a73ad41709e6ebfa675f289e9
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221797B2

Reaction notes

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