Hydrochloric Acid → HCID 46941105, compound

HRID 2410607Notes

Reaction equation

[Cl:1][C:2]1[CH:18]=[C:17]([C:19]2[N:23]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[CH3:36])=[C:26]([CH2:37][O:38][CH3:39])[CH:25]=3)[O:21][N:20]=2)[CH:16]=[CH:15][C:3]=1[CH2:4][N:5]([CH3:14])[CH2:6][C:7]([O:9]C(C)(C)C)=[O:8].Cl>O1CCOCC1>[CH3:39][O:38][CH2:37][C:26]1[CH:25]=[C:24]([C:22]2[O:21][N:20]=[C:19]([C:17]3[CH:16]=[CH:15][C:3]([CH2:4][N:5]([CH3:14])[CH2:6][C:7]([OH:9])=[O:8])=[C:2]([Cl:1])[CH:18]=3)[N:23]=2)[CH:29]=[CH:28][C:27]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH3:36]

Participants

Conditions

Temperature: 80 °C

Procedure

To tert-butyl 2-((2-chloro-4-(5-(2-(methoxymethyl)-2′-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)(methyl)amino)acetate (0.192 g, 0.35 mmol) was added a 4N solution of HCl in dioxane (2 mL) and the reaction mixture stirred at 80° C. for 2 hours. The reaction mixture was concentrated in vacuo. The residue was purified by SCX-2 chromatography eluting with methanol followed by DCM and ammoniacal MeOH (7M) to afford the title compound as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 8.32 (1H, d, J=1.8 Hz), 8.17 (1H, dd, J=7.9, 1.9 Hz), 8.08-8.01 (2H, m), 7.84 (1H, d, J=7.9 Hz), 7.42 (1H, d, J=7.9 Hz), 7.38-7.33 (2H, m), 7.33-7.26 (1H, m), 7.15 (1H, d, J=7.4 Hz), 4.26-4.13 (2H, m), 3.84 (2H, s), 3.25 (3H, s), 2.94 (2H, s), 2.30 (3H, s), 2.04 (3H, s). LC/MS (Method A): 492 (M+H)+. HPLC (Method F) Rt 3.29 min (Purity: 98.0%).

Workup

concentrationThe reaction mixture was concentrated in vacuo
customThe residue was purified by SCX-2 chromatography
washeluting with methanol

Sources & evidence

ORD record: ord-bb7c94a8a4694838b3df12e95021c740
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815919B2

Reaction notes

Loading…