Hydrochloric Acid → HCID 131731802, compound

HRID 2410593Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:19]=[C:18]([C:20]2[N:24]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[CH3:37])=[C:27]([CH2:38][O:39][CH3:40])[CH:26]=3)[O:22][N:21]=2)[CH:17]=[CH:16][C:4]=1[CH2:5][N:6]([CH3:15])[CH2:7][C:8]([O:10]C(C)(C)C)=[O:9].[ClH:41]>O1CCOCC1>[ClH:41].[CH3:1][O:2][C:3]1[CH:19]=[C:18]([C:20]2[N:24]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[CH3:37])=[C:27]([CH2:38][O:39][CH3:40])[CH:26]=3)[O:22][N:21]=2)[CH:17]=[CH:16][C:4]=1[CH2:5][N:6]([CH3:15])[CH2:7][C:8]([OH:10])=[O:9]

Participants

Conditions

Temperature: 70 °C

Procedure

To tert-butyl 2-((2-methoxy-4-(5-(2-(methoxymethyl)-2′-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)(methyl)amino)acetate (52 mg, 0.09 mmol) was added a 4N solution of HCl in dioxane (3 mL) and the mixture was heated in a tube at 70° C. for 3 hours. The solvent was then removed in vacuo to give the title compound as a white solid (36 mg, 78%). 1H NMR (DMSO-d6, 400 MHz) δ 8.28 (1H, s), 8.16 (1, dd, J=7.9, 1.9 Hz), 7.72 (1H, dd, J=7.8, 1.5 Hz), 7.65-7.58 (2H, m), 7.40 (1H, d, J=7.9 Hz), 7.33 (2H, d, J=4.4 Hz), 7.30-7.25 (1H, m), 7.11 (1H, d, J=7.4 Hz), 4.20-4.11 (2H, m), 3.97 (2H, s), 3.91 (3H, s), 3.25-3.20 (5H, m), 2.48 (3H, s), 2.00 (3H, s). LC/MS (Method B): 488 (M+H)+. HPLC (Method F) Rt 3.15 min (Purity: 97.2%).

Workup

customThe solvent was then removed in vacuo

Sources & evidence

ORD record: ord-cbfefb91dd134a26ab87191a3ae3521e
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815919B2

Reaction notes

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