Hydrochloric Acid → HCID 59146027, compound

HRID 1512950Notes

Reaction equation

[OH-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:21]=[C:22]([F:36])[CH:23]=[C:24]4[C:28]=3[NH:27][CH:26]=[C:25]4[CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])[N:16]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])#[N:4].Cl>C1COCC1.O>[C:3]([C:5]1[CH:6]=[C:7]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:21]=[C:22]([F:36])[CH:23]=[C:24]4[C:28]=3[NH:27][CH:26]=[C:25]4[CH2:29][CH2:30][C:31]([OH:33])=[O:32])[N:16]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])#[N:4]

Participants

Conditions

Temperature: 90 °C

Procedure

Sodium hydroxide (100 mg) was added to a solution of ethyl 3-[7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-fluoro-1H-indol-3-yl]propanoate (D138) (230 mg) in THF (4 mL) and water (4 mL). The reaction mixture was stirred at 90° C. for 3 hours. Then 0.5 M HCl was added until pH was about 6. The solvent was concentrated, and the residue was dissolved in water. The precipitate was purified by MDAP and recrystallized in MeCN to afford 3-[7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-fluoro-1H-indol-3-yl]propanoic acid (E99) (135 mg) as an off-white solid. δH (DMSO-d6, 400 MHz): 1.39 (6H, d), 2.63 (2H, t), 2.97 (2H, t), 4.96-5.02 (1H, m), 7.36 (1H, d), 7.55 (1H, d), 7.64-7.69 (2H, m), 8.49 (1H, dd), 8.72 (1H, d), 10.97 (1H, s), 12.13 (1H, br s). δF (DMSO-d6, 376 MHz): −124.9. MS (ES): C23H19FN4O4 requires 434; found 435.2 (M+H+).

Workup

concentrationThe solvent was concentrated
dissolutionthe residue was dissolved in water
customThe precipitate was purified by MDAP
customrecrystallized in MeCN

Sources & evidence

ORD record: ord-6a89a5df4e254617974d8f77e5471413
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217028B2

Reaction notes

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