Hydrochloric Acid → cis-2-(3-Chloro-5-(5-(2-(methoxymethyl)-2'-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)pyridin-2-ylamino)cyclopentanecarboxylic acid

HRID 1631043Notes

Reaction equation

[Cl:1][C:2]1[C:3]([NH:29][C@H:30]2[CH2:34][CH2:33][CH2:32][C@H:31]2[C:35]([O:37]C)=[O:36])=[N:4][CH:5]=[C:6]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[CH3:25])=[C:15]([CH2:26][O:27][CH3:28])[CH:14]=3)[O:10][N:9]=2)[CH:7]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[C:3]([NH:29][C@H:30]2[CH2:34][CH2:33][CH2:32][C@H:31]2[C:35]([OH:37])=[O:36])=[N:4][CH:5]=[C:6]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[CH3:25])=[C:15]([CH2:26][O:27][CH3:28])[CH:14]=3)[O:10][N:9]=2)[CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of methyl cis-2-(3-chloro-5-(5-(2-(methoxymethyl)-2′-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)pyridin-2-ylamino)cyclopentanecarboxylate (0.099 g; 0.19 mmol) in dioxan (2 mL) was added hydrochloric acid (1 mL). The mixture was heated at 60° C. for 24 hours. The solvent was evaporated and the residue purified by preparative HPLC to afford the title compound. 1H NMR (DMSO-d6, 400 MHz) δ 8.76 (1H, d, J=2.0 Hz), 8.33 (1H, s), 8.23-8.14 (2H, s), 7.45-7.26 (4H, m), 7.18 (1H, d, J=7.4 Hz), 6.86 (1H, s), 4.76-4.66 (1H, m), 4.28-4.16 (2H, m), 3.28 (3H, s), 3.11-3.02 (1H, m), 2.15-1.88 (6H, m), 1.88-1.78 (2H, m), 1.71-1.59 (1H, m). LC/MS: 519 (M+H)+. HPLC (Method F) Rt 9.03 min (Purity: 90.9%).

Workup

customThe solvent was evaporated
customthe residue purified by preparative HPLC

Sources & evidence

ORD record: ord-133c78474cb842a6b9172e75656fd4df
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791142B2

Reaction notes

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