Hydrochloric Acid → HCID 44549037, compound

HRID 1512928Notes

Reaction equation

HRID 1512928 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][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[NH:24][CH:23]=[C:22]4[CH2:26][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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59146056HCID 59146056, compound

Product 1

HCID 44549037HCID 44549037, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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]propyl}glycinate (D93) (50 mg) in THF (5 mL) was added aqueous NaOH (2 M, 1 mL). The reaction was stirred at 20° C. overnight. The mixture was acidified with aqueous HCl (2 M) to pH 5-6, partitioned between ethyl acetate (25 mL) and water (10 mL). The organic phase was washed with water (20 mL) and brine (20 mL), dried over anhydrous 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]propyl}glycine (E70) (45 mg, TFA salts). δH (DMSO-d6, 400 MHz): 1.37 (6H, d), 2.02 (2H, m), 2.82 (2H, t), 2.95 (2H, t), 3.69 (2H, s), 4.90 (1H, m), 7.23 (1H, t), 7.31 (1H, d), 7.45 (1H, d), 7.82 (1H, d), 7.95 (1H, d), 8.20 (1H, dd), 8.36 (1H, d), 10.85 (1H, s). MS (ES): C24H26ClN4O4 requires 468; found 469.2 (M+H+).

Workup

  1. custompartitioned between ethyl acetate (25 mL) and water (10 mL)
  2. washThe organic phase was washed with water (20 mL) and brine (20 mL)
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated
  5. customto give the crude product, which
  6. customwas purified by Mass Directed Auto Prep

Sources & evidence

ORD record
ord-5e1a904044d440b0a8704c868dc92c67
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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