Hydrochloric Acid → HCID 46908238, compound

HRID 1631028Notes

Reaction equation

[CH3:1][N:2]([CH2:11][C:12]1[CH:17]=[C:16]([C:18]2[N:22]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]4[CH3:35])=[C:25]([C:36]([F:39])([F:38])[F:37])[CH:24]=3)[O:20][N:19]=2)[CH:15]=[CH:14][N:13]=1)[CH2:3][C:4]([O:6]C(C)(C)C)=[O:5].Cl>O1CCOCC1>[CH3:1][N:2]([CH2:11][C:12]1[CH:17]=[C:16]([C:18]2[N:22]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]4[CH3:35])=[C:25]([C:36]([F:39])([F:38])[F:37])[CH:24]=3)[O:20][N:19]=2)[CH:15]=[CH:14][N:13]=1)[CH2:3][C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 70 °C

Procedure

To tert-butyl 2-(methyl((4-(5-(4-(2-methylpiperidin-1-yl)-3-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)methyl)amino)acetate (0.056 g; 0.10 mmol) was added HCl solution in dioxan (4 M; 3 mL) and the reaction mixture stirred at 70° C. for 4 hours. The solvent was evaporated in vacuo and the residue purified by preparative HPLC, affording the title product as a brown oil. 1H NMR (CDCl3, 400 MHz) δ 8.79 (1 H, d, J=5.1 Hz), 8.49 (1 H, d, J=2.1 Hz), 8.33 (1 H, dd, J=8.4, 2.1 Hz), 8.04-8.00 (2 H, m), 7.55 (1 H, d, J=8.4 Hz), 4.11 (2 H, s), 3.50 (2 H, s), 3.15-3.01 (2 H, m), 2.62 (3 H, s), 2.62-2.54 (1 H, m), 1.90-1.44 (6 H, m), 0.86 (3 H, d, J=6.2 Hz). LC/MS: 490 (M+H)+. HPLC (Method B) Rt 3.46 min (Purity: 98.9%).

Workup

customThe solvent was evaporated in vacuo
customthe residue purified by preparative HPLC

Sources & evidence

ORD record: ord-96675566b9794505aca38d881fea2bff
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791142B2

Reaction notes

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