HCID 68156576, compound → HCID 178440885, compound

HRID 877356Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([NH:14][C@@H:15]([C:28]2[N:29]=[N:30][N:31](CC3C=CC(OC)=CC=3)[CH:32]=2)[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:18][N:17]=2)=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)(C(F)(F)F)=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:12]([NH:14][C@@H:15]([C:28]2[N:29]=[N:30][NH:31][CH:32]=2)[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:27])([F:25])[F:26])=[CH:18][N:17]=2)=[O:13])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 65 °C

Procedure

2-(4-tert-butylphenyl)-N-{(S)-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl][5-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}acetamide (0.064 g, 0.11 mmol) was dissolved in TFA (1.0 mL) and heated at 65° C. for 6 h. The solvent was removed by N2 and the residue was purified by reverse-phase HPLC to give the product (0.046 g, 91%). 1H NMR (CDCl3, 400 MHz) δ 8.30 (d, J=2.8 Hz, 1H), 7.94 (d, J=6.8 Hz, 1H), 7.49 (s, 1H), 7.45 (d, J=8.8 Hz, 1H), 7.39 (dd, J=2.8, 8.8 Hz, 1H), 7.34 (d, J=8.4 Hz, 2H), 7.20 (d, J=8.4 Hz, 2H), 6.39 (d, J=6.8 Hz, 1H), 4.41 (q, J=8.0 Hz, 2H), 3.63 (s, 2H), 1.30 (s, 9H). HRMS (ES) [M+1]+ calcd for C22H24F3N5O2: 448.1955. Found: 448.1976.

Workup

customThe solvent was removed by N2
customthe residue was purified by reverse-phase HPLC

Sources & evidence

ORD record: ord-861d4747e3de438e8d670536a3ef3d0c
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987310B2

Reaction notes

Loading…