Water → HCID 66676945, compound

HRID 423375Notes

Reaction equation

HRID 423375 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:8]=[C:7]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3[CH:16]=[CH:17][N:18]4[CH2:23][CH2:24][C:25]([O:27]CC)=[O:26])[N:10]=2)[CH:6]=[CH:5][C:4]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[OH-].[Na+:39].O>C(O)C>[F:37][C:2]([F:1])([F:36])[C:3]1[CH:8]=[C:7]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3[CH:16]=[CH:17][N:18]4[CH2:23][CH2:24][C:25]([O-:27])=[O:26])[N:10]=2)[CH:6]=[CH:5][C:4]=1[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1.[Na+:39]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 59318373HCID 59318373, compound

Product 1

HCID 66676945HCID 66676945, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

Ethyl 3-(4-{5-[2-(trifluoromethyl)-4-biphenylyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate (D64) (15 mg, 0.31 mmol) was dissolved in ethanol (50 ml) by warming to 40° C. for 10 minutes then 2N sodium hydroxide (4 ml, 8 mmol) was added followed by water (8 ml). The solution was left standing for 1 hour. Evaporated off the ethanol and filtered off the off-white solid. Mass of title compound as a beige obtained on drying was 42 mg. δH (400 MHz, methanol-d4) 2.69 (2H, t), 4.53 (2H, t), 7.17-7.18 (1H, m), 7.32-7.40 (3H, m), 7.46-4.49 (4H, m), 7.66 (1H, d), 7.75 (1H, d), 8.02 (1H, d), 8.53 (1H, dd), 8.63 (1H, d). MS (ES) C26H18F3N3O3 requires 477; found 478 (MH+).

Workup

  1. waitThe solution was left
  2. customEvaporated off the ethanol
  3. filtrationfiltered off the off-white solid

Sources & evidence

ORD record
ord-1268a9a445424b9ba35eed0c60b9f09f
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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