Trifluoroacetic acid → HCID 11699803, compound

HRID 2367839Notes

Reaction equation

C(OC(=O)[NH:7][C:8]([CH3:48])([CH3:47])[C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]([C:26]3[N:27](COCC[Si](C)(C)C)[CH:28]=[C:29]([C:31]#[N:32])[N:30]=3)=[O:25])=[C:19]([C:41]3[CH2:46][CH2:45][CH2:44][CH2:43][CH:42]=3)[CH:18]=2)[CH2:13][CH2:12]1)=[O:10])(C)(C)C.[C:50]([OH:56])([C:52]([F:55])([F:54])[F:53])=[O:51]>C(Cl)Cl.CCO>[F:53][C:52]([F:55])([F:54])[C:50]([OH:56])=[O:51].[NH2:7][C:8]([CH3:48])([CH3:47])[C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]([C:26]3[NH:30][C:29]([C:31]#[N:32])=[CH:28][N:27]=3)=[O:25])=[C:19]([C:41]3[CH2:46][CH2:45][CH2:44][CH2:43][CH:42]=3)[CH:18]=2)[CH2:13][CH2:12]1)=[O:10]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of {2-[4-(4-{[4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbonyl]-amino}-3-cyclohex-1-enyl-phenyl)-piperidin-1-yl]-1,1-dimethyl-2-oxo-ethyl}-carbamic acid tert-butyl ester (40 mg, 0.050 mmol) in 2 mL of DCM and 20 μL of EtOH was added 1.5 mL of TFA. The solution was stirred for 3 h at 25° C., diluted with 2 mL of EtOH and concentrated in vacuo. Trituration of the residue with ether afforded 8.4 mg (29%) of the title compound as a white solid. 1H-NMR (CD3OD; 400 MHz): δ 8.10 (d, 1H, J=8.4 Hz), 8.00 (s, 1H), 7.16 (d, 1H, J=8.4 Hz), 7.07 (s, 1H), 5.79 (s, 1H), 4.55-4.48 (m, 1H), 3.30 (s, 6H), 2.89-2.87 (m, 2H), 2.40-2.25 (m, 4H), 1.96-1.93 (m, 2H), 1.86-1.83 (m, 6H), 1.64-1.61 (m, 2H). Mass Spectrum (ESI, m/z): Calcd. for C26H33N6O2, 461.2 (M+H). found 461.3.

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b9cf26a2f59c40c3a9e4d4bc081dcea5
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697716B2

Reaction notes

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