Sodium Hydroxide → Sodium 3-(3-chloro-5-{5-[6-(methyloxy)-3-biphenylyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate

HRID 423379Notes

Reaction equation

HRID 423379 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:15]=[C:14]([C:16]4[CH:17]=[C:18]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[C:19]([O:22][CH3:23])=[CH:20][CH:21]=4)[O:13][N:12]=3)[CH:9]=2)[N:4]([CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])[CH:3]=1.[OH-].[Na+:38]>C(O)C>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:15]=[C:14]([C:16]4[CH:17]=[C:18]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[C:19]([O:22][CH3:23])=[CH:20][CH:21]=4)[O:13][N:12]=3)[CH:9]=2)[N:4]([CH2:30][CH2:31][C:32]([O-:34])=[O:33])[CH:3]=1.[Na+:38]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59318433Ethyl 3-(3-chloro-5-{5-[6-(methyloxy)-3-biphenylyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate

Product 1

HCID 66677416Sodium 3-(3-chloro-5-{5-[6-(methyloxy)-3-biphenylyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 3-(3-chloro-5-{5-[6-(methyloxy)-3-biphenylyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate (D107) (90 mg, 0.18 mmol) was heated in ethanol (10 ml) to give a clear solution. This solution was treated with 2N sodium hydroxide (3 ml, 6 mmol) and stirred at 50° C. for 30 minutes. Evaporated off the ethanol and filtered off the white solid that precipitated out of solution, washing the solid with a small amount of water and ether. Stirred solid in a small amount of acetone for 1 hour, filtered, washed with a small amount of ether and dried to yield the title compound as 45 mg of white solid. δH (400 MHz, d6-DMSO) 2.34 (2H, t), 3.91 (3H, s), 4.34 (2H, t), 7.41-7.46 (2H, m), 7.48-7.50 (2H, m), 7.57-7.59 (2H, m), 7.63-7.66 (2H, m), 7.80 (1H, d), 8.10 (1H, d), 8.10-8.25 (2H, m). MS (ES) C26H2035ClN3O4 requires 473; found 474 (MH+).

Workup

  1. customto give a clear solution
  2. customEvaporated off the ethanol
  3. filtrationfiltered off the white solid
  4. customthat precipitated out of solution
  5. washwashing the solid with a small amount of water and ether
  6. stirringStirred solid in a small amount of acetone for 1 hour
  7. filtrationfiltered
  8. washwashed with a small amount of ether
  9. customdried

Sources & evidence

ORD record
ord-786f043a41294ee3a8299256a4987b76
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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