Hydrochloric Acid → HCID 44547324, compound

HRID 1512960Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:26]=[C:25]4[C:21]([C:22]([CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])=[CH:23][NH:24]4)=[CH:20][C:19]=3[F:34])[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].[OH-].[Na+].Cl>C(O)(C)C.O>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:26]=[C:25]4[C:21]([C:22]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:23][NH:24]4)=[CH:20][C:19]=3[F:34])[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of ethyl 3-[6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-fluoro-1H-indol-3-yl]propanoate (D157) (180 mg) in isopropanol (25 mL) and water (5 mL) was added 0.8 mL 20% aqueous NaOH solution. The reaction mixture was stirred at 20° C. overnight. Afterwards, the mixture was adjusted to pH 3 by addion of 6 M HCl and evaporated. The residue was treated with 6 mL DMF and filtered. The filtrate was purified by MDAP to give the designed product 3-[6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-fluoro-1H-indol-3-yl]propanoic acid (E110) (115 mg). δH (DMSO-d6, 400 MHz): 1.32 (6H, d), 2.55 (2H, t), 2.88 (2H, t), 4.92 (1H, m), 7.37 (1H, s), 7.47 (1H, d), 7.50 (1H, d), 8.05 (1H, d), 8.35 (1H, dd), 8.44 (1H, d), 11.23 (1H, s), 12.05 (1H, s); δF (DMSO-d6, 376 MHz): −121.7; MS (ES): C23H19FN4O4 requires 434; found 435.2 (M+H+).

Workup

customevaporated
additionThe residue was treated with 6 mL DMF
filtrationfiltered
customThe filtrate was purified by MDAP

Sources & evidence

ORD record: ord-e4c60fad54dc4be980d32299eeb92fef
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217028B2

Reaction notes

Loading…