Hydrochloric Acid → HCID 58554079, compound

HRID 1631036Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[CH:17][C:18]([CH2:21][N:22]([CH3:31])[CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])=[N:19][CH:20]=3)[N:11]=2)[CH:7]=[CH:6][C:5]=1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH3:38].Cl>O1CCOCC1>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[CH:17][C:18]([CH2:21][N:22]([CH3:31])[CH2:23][C:24]([OH:26])=[O:25])=[N:19][CH:20]=3)[N:11]=2)[CH:7]=[CH:6][C:5]=1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH3:38]

Participants

Conditions

Temperature: 80 °C

Procedure

To tert-butyl N-[(5-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}pyridin-2-yl)methyl]-N-methylglycinate (0.550 g; 1.07 mmol) was added HCl solution in dioxan (4 M; 15 mL) and the reaction mixture stirred at ambient temperature for 2 hours and at 80° C. for 1 hour. The reaction mixture was allowed to cool and the suspension was filtered. The solid was washed with ether and dried under vacuum. The residue was triturated with DCM to afford the title compound as an off-white solid (0.420 g, 74%). 1H NMR (DMSO-d6/D2O, 400 MHz) δ 9.31 (1 H, s), 8.58-8.55 (1 H, dd, J=8, 2 Hz), 8.30 (1 H, J=2 Hz), 8.19-8.16 (1 H, m), 7.77 (1 H, d, J=7.6 Hz), 7.42-7.26 (4 H, m), 7.11-7.10 (1 H, m), 4.65 (2 H, s), 4.26-4.12 (4 H, m), 3.21 (3 H, s), 2.92 (3 H, s), 2.00 (3 H, s). LC/MS: 459 (M+H)+. HPLC (Method D) Rt 8.60 min (Purity: 98.5%).

Workup

temperatureto cool
filtrationthe suspension was filtered
washThe solid was washed with ether
customdried under vacuum
customThe residue was triturated with DCM

Sources & evidence

ORD record: ord-66208f0e74bc4b9395208dbb72d5f710
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791142B2

Reaction notes

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