Triethylamine → HCID 178510398, compound

HRID 1428013Notes

Reaction equation

FC(F)(F)C(O)=O.[C:8]1([C:14]2[CH:19]=[C:18]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH:17]=[CH:16][C:15]=2[NH:26][C:27]([C:29]2[NH:30][CH:31]=[C:32]([C:34]#[N:35])[N:33]=2)=[O:28])[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=1.CCN(CC)CC.C[Si]([N:47]=[C:48]=[O:49])(C)C>C(Cl)Cl>[C:34]([C:32]1[N:33]=[C:29]([C:27]([NH:26][C:15]2[CH:16]=[CH:17][C:18]([CH:20]3[CH2:21][CH2:22][N:23]([C:48]([NH2:47])=[O:49])[CH2:24][CH2:25]3)=[CH:19][C:14]=2[C:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=2)=[O:28])[NH:30][CH:31]=1)#[N:35]

Participants

Conditions

Temperature: 25 °C

Procedure

A flask was charged with 4-cyano-1H-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide TFA salt (51 mg, 0.10 mmol) (as prepared in Example 14, step (b)), NEt3 (22 μL, 0.15 mmol), trimethylsilyl isocyanate (16 μL, 0.11 mmol) and 1.0 mL of DCM and stirred for 10 h at 25° C. The solvent was evaporated and the title compound was purified by RP-HPLC (C18), eluting with 35-60% CH3CN in 0.1% TFA/H2O over 11 min to give 30 mg (70%) of a white solid. 1H-NMR (400 MHz, DMSO-d6): δ 14.28 (br s, 1H), 9.76 (s, 1H), 8.34 (s, 1H), 7.84 (d, 1H), 7.18 (dd, 1H), 7.08 (d, 1H), 6.00 (br s, 2H), 5.72 (m, 1H), 4.18 (m, 2H), 2.80-2.60 (m, 3H), 2.24-2.10 (m, 4H), 1.80-1.60 (m, 6H), 1.50 (m, 2H). Mass spectrum (ESI, m/z): Calcd. for C23H26N6O, 419.2 (M+H). found 419.0.

Workup

customThe solvent was evaporated
customthe title compound was purified by RP-HPLC (C18)
washeluting with 35-60% CH3CN in 0.1% TFA/H2O over 11 min

Sources & evidence

ORD record: ord-f8aa1101b40248e79898eae6c38eb23f
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933091B2

Reaction notes

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