Trifluoroacetic acid → 4-Cyano-1H-imidazole-2-carboxylic acid [4-(1-azido-1-methyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amide

HRID 1508019Notes

Reaction equation

[C:1]1([C:7]2[CH:12]=[C:11]([C:13](O)([CH3:15])[CH3:14])[CH:10]=[CH:9][C:8]=2[NH:17][C:18]([C:20]2[NH:21][CH:22]=[C:23]([C:25]#[N:26])[N:24]=2)=[O:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[N-:27]=[N+:28]=[N-:29].[Na+].C(O)(C(F)(F)F)=O.CCOC(C)=O>C(Cl)(Cl)Cl>[N:27]([C:13]([C:11]1[CH:10]=[CH:9][C:8]([NH:17][C:18]([C:20]2[NH:21][CH:22]=[C:23]([C:25]#[N:26])[N:24]=2)=[O:19])=[C:7]([C:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=2)[CH:12]=1)([CH3:15])[CH3:14])=[N+:28]=[N-:29]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 4-cyano-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-amide (as prepared in example 1, step (h), 15.0 mg, 0.0428 mmol) and NaN3 (27.8 mg, 0.428 mmol) in 1 mL of chloroform at 0° C. under Ar was added TFA (49 μL, 0.64 mmol). The resulting mixture was stirred at 0° C. for 1 h under Ar. Treated with 30 mL of EtOAc, the mixture was washed with saturated aqueous NaHCO3 (10 mL), brine (10 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (0-5% EtOAc/DCM) gave 13.6 mg (84%) of the title compound as a white solid. Mass spectrum (ESI, m/z): Calcd. for C20H21N7O, 376.2 (M+H). found 376.0.

Workup

washthe mixture was washed with saturated aqueous NaHCO3 (10 mL), brine (10 mL)
dry with materialdried (Na2SO4)
customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record: ord-201901924f3b4aaa826a3f2816090966
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221797B2

Reaction notes

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