Hydrochloric Acid → HCID 68649418, compound

HRID 219576Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[C:11]([C:19]2[O:23][N:22]=[C:21]([CH:24]3[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]3)[N:20]=2)[N:10]=[N:9]1.[ClH:37]>CO>[ClH:37].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)=[C:11]([C:19]2[O:23][N:22]=[C:21]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[N:20]=2)[N:10]=[N:9]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of tert-butyl 4-(5-(1-(2-fluorophenyl)-5-(pyridin-4-yl)-1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate, obtained in Step 1, (601 mg; 1.22 mmol) in MeOH (30 mL) was added HCl (3 M, 30 mL) and the mixture was heated at 50° C. for 5 hours. The solvent was removed in vacuo affording the title compound as a white solid (462 mg; 96%). 1H NMR: (DMSO-d6, 400 MHz) δ 9.38-9.36 (1H, m), 9.26-9.24 (1H, m), 8.88 (2H, d, J=5.4 Hz), 7.94-7.84 (3H, m), 7.76-7.69 (1H, m), 7.55-7.46 (2H, m), 3.34-3.24 (3H, m), 3.06 (2H, q, J=11.1 Hz), 2.14 (2H, d, J=13.8 Hz), 2.04-1.90 (2H, m). LC/MS (Method C): 392 (M+H)+. HPLC (Method E) Rt 2.14 min (Purity: 97.5%).

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-e75981fe10cf4005af7345d903f55263
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202856B2

Reaction notes

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