Trifluoroacetic acid → HCID 178473857, compound

HRID 536927Notes

Reaction equation

[C:1]([N:4]1[CH2:9][CH2:8][C:7]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]3[NH:21][CH:22]=[C:23]([C:25]#[N:26])[N:24]=3)=[O:19])=[C:13]([C:27]3[CH2:32][CH2:31][C:30]([CH3:34])([CH3:33])[CH2:29][CH:28]=3)[CH:12]=2)(O)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[N-:35]=[N+:36]=[N-:37].[Na+].C(O)(C(F)(F)F)=O.CCOC(C)=O>C(Cl)Cl>[C:1]([N:4]1[CH2:9][CH2:8][C:7]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]3[NH:21][CH:22]=[C:23]([C:25]#[N:26])[N:24]=3)=[O:19])=[C:13]([C:27]3[CH2:32][CH2:31][C:30]([CH3:34])([CH3:33])[CH2:29][CH:28]=3)[CH:12]=2)([N:35]=[N+:36]=[N-:37])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 4-cyano-1H-imidazole-2-carboxylic acid [4-(1-acetyl-4-hydroxy-piperidin-4-yl)-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (as prepared in Example 35, 40.0 mg, 0.0867 mmol) and NaN3 (56.3 mg, 0.0867 mmol) in 2 mL of DCM at 0° C. under Ar was added TFA (100 μL, 1.30 mmol). The resulting mixture was stirred at 0° C. for 0.5 h, at RT for 2 d under Ar. Treated with 20 mL of EtOAc, the mixture was washed with saturated NaHCO3 aqueous solution (10 mL), brine (5 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (1-3% MeOH/DCM) gave 40.0 mg (95%) of the title compound as a white solid. Mass spectrum (ESI, m/z): Calcd. for C26H30N8O2, 487.3 (M+H). found 487.0.

Workup

washthe mixture was washed with saturated NaHCO3 aqueous solution (10 mL), brine (5 mL)
dry with materialdried (Na2SO4)
customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record: ord-2967f2bdd16c4b1ea2c991a538a9e716
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859602B2

Reaction notes

Loading…