Hydrochloric Acid → HCID 44548891, compound

HRID 1512922Notes

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[N:24]([CH3:26])[CH:23]=[C:22]4[CH2:27][CH2:28][NH:29][CH2:30][C:31]([O:33]CC)=[O:32])[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[N:24]([CH3:26])[CH:23]=[C:22]4[CH2:27][CH2:28][NH:29][CH2:30][C:31]([OH:33])=[O:32])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl N-{2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]ethyl}glycinate (D89) (20 mg) in THF (5 mL) was added aqueous NaOH (2 M, 1 mL). The reaction was stirred at 50° C. for 3 h. The mixture was cooled to room temperature and acidified with aqueous HCl (2 M) to pH 4-5. The mixture was partitioned between ethyl acetate (25 mL) and water (20 mL). The organic phase was evaporated to give the crude product, which was purified by Mass Directed Auto Prep to afford N-{2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]ethyl}glycine (E64) (13 mg, TFA salt). δH (DMSO-d6, 400 MHz): 1.36 (6H, d), 3.10 (2H, t), 3.24 (2H, t), 3.65 (3H, s), 3.87 (2H, s), 4.88 (1H, m), 7.22 (1H, t), 7.30 (1H, s), 7.45 (1H, d), 7.47 (1H, dd), 7.83 (1H, dd), 8.12 (1H, dd), 8.18 (1H, d). MS (ES): C24H26ClN4O4 requires 468; found 469.2 (M+H+).

Workup

temperatureThe mixture was cooled to room temperature
customThe mixture was partitioned between ethyl acetate (25 mL) and water (20 mL)
customThe organic phase was evaporated
customto give the crude product, which
customwas purified by Mass Directed Auto Prep

Sources & evidence

ORD record: ord-8d8f2f6251af4312904550d918b2cdf0
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217028B2

Reaction notes

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