Sodium Hydroxide → Sodium 3-(5-{5-[3-chloro-4-(ethyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indazol-1-yl)propanoate

HRID 2189809Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

Ethyl 3-(5-{5-[3-chloro-4-(ethyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indazol-1-yl)propanoate (D57) (77 mg, 0.17 mmol) was suspended in 2M aq. NaOH (2 ml) and ethanol (2 ml). The mixture was heated at 50° C. until dissolved then cooled. The ethanol was removed in vacuo and the resultant solid was filtered, washed with ethanol, water and diethyl ether then dried under high vacuum to afford the title compound (63.6 mg) as a pink solid. δH (methanol-d4, 400 MHz) 1.49 (3H, t), 2.77 (2H, t), 4.25 (2H, q), 4.71 (2H, t), 7.27 (1H, d), 7.82 (1H, d), 8.09-8.25 (4H, m), 8.55 (1H, s). MS (ES): C20H1735ClN4O4 requires; 412 found (MH+) 413.

Workup

dissolutionuntil dissolved
temperaturethen cooled
customThe ethanol was removed in vacuo
filtrationthe resultant solid was filtered
washwashed with ethanol, water and diethyl ether
customthen dried under high vacuum

Sources & evidence

ORD record: ord-52c92034f03f4134a1d2d6053d5421db
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324254B2

Reaction notes

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