Trifluoroacetic acid → HCID 178473857, compound

HRID 1054245Notes

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-5fd7eb9584054ef9a37107e6f589fa2f
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394289B2

Reaction notes

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