Hydrochloric Acid → HCID 44547323, compound

HRID 1512959Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of ethyl 3-[6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-fluoro-1H-indol-3-yl]propanoate (D156) (120 mg) in isopropanol (25 mL) and water (5 mL) was added 0.5 mL of 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-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-fluoro-1H-indol-3-yl]propanoic acid (E109) (45 mg). δH (DMSO-d6, 400 MHz): 1.30 (6H, d), 2.59 (2H, t), 2.88 (2H, t), 4.82 (1H, m), 7.37 (1H, s), 7.38 (1H, d), 7.48 (1H, d), 8.04 (1H, dd), 8.06 (1H, d), 8.12 (1H, d), 11.20 (1H, s); δF (DMSO-d6, 376 MHz): −121.5; MS (ES): C22H19ClFN3O4 requires 443.1; found 444.2 (M+H+).

Workup

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

Sources & evidence

ORD record: ord-664cdc6a389c4f36882517b20b87eed0
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217028B2

Reaction notes

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