Hydrochloric Acid → HCID 44546857, compound

HRID 1512931Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][CH:23]=[C:22]4[CH2:26][CH2:27][C:28]([NH:30][CH2:31][C:32]([O:34]CC)=[O:33])=[O:29])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][CH:23]=[C:22]4[CH2:26][CH2:27][C:28]([NH:30][CH2:31][C:32]([OH:34])=[O:33])=[O:29])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of ethyl N-{3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoyl}glycinate (D125) (150 mg) in THF (15 mL) was added aqueous NaOH (2 M, 2 mL). The reaction was stirred at 20° C. for 3 h. The mixture was acidified with aqueous HCl (2 M) to pH 5-6, partitioned between ethyl acetate (50 mL) and water (25 mL). The organic phase was dried over sodium sulphate and evaporated to give the crude product, which was purified by Mass Directed Auto Prep to afford N-{3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoyl}glycine (E77) (120 mg). δH (DMSO-d6, 400 MHz): 1.36 (6H, d), 2.56 (2H, t), 2.99 (2H, t), 3.76 (2H, d), 4.89 (1H, m), 7.21 (1H, t), 7.27 (1H, s), 7.44 (1H, d), 7.82 (1H, d), 7.93 (1H, d), 8.20 (2H, m), 8.37 (1H, d), 10.78 (1H, s), 12.46 (1H, s). MS (ES): C24H23ClN4O6 requires 482; found 483.2 (M+H+).

Workup

custompartitioned between ethyl acetate (50 mL) and water (25 mL)
dry with materialThe organic phase was dried over sodium sulphate
customevaporated
customto give the crude product, which
customwas purified by Mass Directed Auto Prep

Sources & evidence

ORD record: ord-908139f928e64f5ca37b23a57e666580
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217028B2

Reaction notes

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