Sodium Hydroxide → HCID 86603006, compound

HRID 735446Notes

Reaction equation

HRID 735446 reaction equation
[F:1][C:2]1[CH:38]=[C:37]([F:39])[CH:36]=[C:35]([F:40])[C:3]=1[CH2:4][N:5]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][CH2:23][C@H:22]([CH2:26][C:27]([O:29]C)=[O:28])[CH2:21]3)=[CH:16][CH:15]=2)=[C:12]2[C:7]([C:8]([C:31]([F:34])([F:33])[F:32])=[CH:9][CH:10]=[CH:11]2)=[N:6]1.[OH-].[Na+]>CO.C1COCC1>[F:40][C:35]1[CH:36]=[C:37]([F:39])[CH:38]=[C:2]([F:1])[C:3]=1[CH2:4][N:5]1[C:13]([C:14]2[CH:15]=[CH:16][C:17]([N:20]3[CH2:25][CH2:24][CH2:23][C@H:22]([CH2:26][C:27]([OH:29])=[O:28])[CH2:21]3)=[CH:18][CH:19]=2)=[C:12]2[C:7]([C:8]([C:31]([F:34])([F:32])[F:33])=[CH:9][CH:10]=[CH:11]2)=[N:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86603007HCID 86603007, compound

Product 1

HCID 86603006HCID 86603006, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of methyl ((3R)-1-{4-[2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-yl]phenyl}piperidin-3-yl)acetate (0.045 g, 0.08 mmol) in CH3OH-THF (1:1, v/v) containing 0.5 mL of 1 N NaOH was stirred overnight at ambient temperature. Then it was neutralized with dilute acid and partitioned with ethyl acetate and brine. The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude product was crystallized from ether/petroleum ether to give 0.036 g of title compound as a pale yellow solid.

Workup

  1. additionwith dilute acid
  2. custompartitioned with ethyl acetate and brine
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was crystallized from ether/petroleum ether

Sources & evidence

ORD record
ord-29cb6b7cfaa641d7aab0034e20d2f23c
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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