Sodium Hydroxide → HCID 45112076, compound

HRID 1678697Notes

Reaction equation

HRID 1678697 reaction equation
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH2:13][CH:14]([C:21]2[N:22]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[N:23]=[C:24]3[C:29]=2[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[OH-].[Na+]>CO.O>[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([N:22]2[C:21]([CH:14]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:13][S:10]([C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:37])=[O:2])=[CH:9][CH:8]=3)(=[O:12])=[O:11])=[C:29]3[C:24]([CH2:25][CH2:26][CH2:27][CH2:28]3)=[N:23]2)=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67131122HCID 67131122, compound

Product 1

HCID 45112076HCID 45112076, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of [rac]-4-{2-[2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-2-cyclohexyl-ethanesulfonyl}-benzoic acid methyl ester (40 mg, 0.076 mmol) in MeOH (5 ml) was added NaOH (5.18 mg, 0.129 mmol) in water (2 ml) dropwise at 0° C. The reaction mixture was then stirred at 25° C. for 14 h. After the completion of the reaction (monitored through TLC), MeOH was concentrated in vacuo, diluted with H2O (5 ml) and the aqueous layer was acidified (pH ˜2-3) with 2 N HCl, and then extracted with EtOAc (3×5 ml). Combined organic layers were washed with brine (10 ml) and finally dried over Na2SO4. Organic layer was distilled under reduced pressure to get crude title compound (32 mg). Purification was done by column chromatography over silica gel (230-400 mesh; 2% MeOH/DCM) to give the title compound (18 mg, 47.1%) as an off white solid. MS: m/e=527.2 [M+H+].

Workup

  1. concentrationwas concentrated in vacuo
  2. additiondiluted with H2O (5 ml)
  3. extractionextracted with EtOAc (3×5 ml)
  4. washCombined organic layers were washed with brine (10 ml)
  5. dry with materialfinally dried over Na2SO4
  6. distillationOrganic layer was distilled under reduced pressure
  7. customto get crude title compound (32 mg)
  8. customPurification

Sources & evidence

ORD record
ord-5413f894446f4d9c8dd8091974f7327e
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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