Hydrochloric Acid → HCID 44546860, compound

HRID 1512934Notes

Reaction equation

HRID 1512934 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][CH2:29][O:30][CH2:31][C:32]([O:34]CC)=[O:33])[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][CH2:29][O:30][CH2:31][C:32]([OH:34])=[O:33])[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 59146110HCID 59146110, compound

Product 1

HCID 44546860HCID 44546860, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of ethyl ({3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]propyl}oxy)acetate (D105) (80 mg) in THF (10 mL) was added 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 4-5, partitioned between ethyl acetate (25 mL) and water (25 mL). The organic phase was washed with water (25 mL) and brine (25 mL), dried over anhydrous sodium sulphate and evaporated to give the crude product, which was purified by Mass Directed Auto Prep to afford ({3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]propyl}oxy)acetic acid (E80) (50 mg). δH (DMSO-d6, 400 MHz): 1.35 (6H, d), 1.89 (2H, m), 2.49 (2H, t), 3.52 (2H, t), 3.63 (3H, s), 4.01 (2H, s), 4.87 (1H, m), 7.17 (2H, m), 7.42 (2H, m), 7.77 (1H, dd), 8.12 (1H, dd), 8.19 (1H, d), 12.56 (1H, br s). MS (ES): C25H26ClN3O5 requires 483; found 484.2 (M+H+).

Workup

  1. custompartitioned between ethyl acetate (25 mL) and water (25 mL)
  2. washThe organic phase was washed with water (25 mL) and brine (25 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-95e4ec3d555c4c93b4e185c7bb21b95a
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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