Sodium Hydroxide → HCID 25062823, compound

HRID 2189812Notes

Reaction equation

HRID 2189812 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21]([CH2:25][CH2:26][C:27]([O:29]CC)=[O:28])[N:20]=[CH:19]4)[N:12]=2)=[CH:7][C:6]=1[C:32]([F:35])([F:34])[F:33])[CH3:3].[OH-].[Na+]>C(O)C>[CH3:3][CH:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])[N:20]=[CH:19]4)[N:12]=2)=[CH:7][C:6]=1[C:32]([F:34])([F:35])[F:33])[CH3:1]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59316697HCID 59316697, compound

Product 1

HCID 25062823HCID 25062823, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-(5-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indazol-1-yl)propanoate (D59) (82 mg, 0.17 mmol) was dissolved in ethanol (4 ml) and then 2M aq. NaOH added (0.5 ml). The reaction was stirred at room temperature overnight and then the ethanol was evaporated in vacuo. Ethyl acetate was added but as the compound appeared to be in both aqueous and organic layers the mixture was evaporated. Purification by MDAP (in two batches) followed by freeze-drying gave the title compound (28.7 mg). δH (400 MHz, d6-DMSO) 1.36 (6H, d), 2.88 (2H, t), 4.65 (2H, t), 4.98 (1H, sept.), 7.59 (1H, d), 7.89 (1H, d), 8.07 (1H, dd), 8.27 (1H, d), 8.32 (1H, d), 8.41 (1H, dd), 8.57 (1H, dd). MS (ES): C22H19F3N4O4 requires 460; found (MH+) 461.

Workup

  1. customthe ethanol was evaporated in vacuo
  2. additionEthyl acetate was added but as the compound
  3. customwas evaporated
  4. customPurification by MDAP (in two batches)
  5. customby freeze-drying

Sources & evidence

ORD record
ord-c55973503682422993019a57e3ae5970
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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