Hydrochloric Acid → HCID 131731760, compound

HRID 2404365Notes

Reaction equation

[F: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]([C:37]([F:40])([F:39])[F:38])[CH:25]=3)[O:21][N:20]=2)[CH:16]=[C:15]([F:41])[C:3]=1[CH2:4][N:5]([CH3:14])[CH2:6][C:7]([O:9]C(C)(C)C)=[O:8].[ClH:42]>O1CCOCC1>[ClH:42].[F:41][C:15]1[CH:16]=[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]([C:37]([F:38])([F:40])[F:39])[CH:25]=3)[O:21][N:20]=2)[CH:18]=[C:2]([F:1])[C:3]=1[CH2:4][N:5]([CH3:14])[CH2:6][C:7]([OH:9])=[O:8]

Participants

Conditions

Temperature: 70 °C

Procedure

To tert-butyl 2-((2,6-difluoro-4-(5-(2′-methyl-2-(trifluoromethyl)biphenyl-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)(methyl)amino)acetate (0.101 g, 0.18 mmol) was added a 4N solution of HCl in dioxane (4.5 mL) and the reaction mixture stirred at 70° C. for 1 hour. The reaction mixture was allowed to cool and the solvent evaporated in vacuo. The residue was triturated with ACN to afford the title compound (0.087 g, 87%). 1H NMR (DMSO-d6, 400 MHz) δ 8.60 (1H, d, J=1.7 Hz), 8.55 (1H, dd, J=8.0, 1.7 Hz), 7.98 (2H, d, J=7.7 Hz), 7.72 (1H, d, J=8.0 Hz), 7.45-7.38 (2H, m), 7.33 (1H, ddd, J=7.6, 6.5, 2.3 Hz), 7.20 (1H, d, J=7.6 Hz), 4.51 (2H, br s), 4.15 (2H, br s), 2.81 (3H, br s), 2.06 (3H, br s). LC/MS (Method A): 518 (M+H)+. HPLC (Method F) Rt 3.38 min (Purity: 99.5%).

Workup

temperatureto cool
customthe solvent evaporated in vacuo
customThe residue was triturated with ACN

Sources & evidence

ORD record: ord-896660b55e0949ee974213b7db540cc4
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802704B2

Reaction notes

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