Hydrochloric Acid → HCID 58088352, compound

HRID 250294Notes

Reaction equation

HRID 250294 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]4[C:23]([C:30]5[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=5[Cl:37])=[N:24][O:25][C:26]=4[CH:27]([CH3:29])[CH3:28])=[CH:16][C:15]=3[CH3:38])=[CH:11][CH:12]=2)[N:7]([CH:39]([CH3:41])[CH3:40])[C:6]=1[CH3:42])=[O:4].[OH-].[Na+].Cl>CO>[Cl:36][C:35]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:37])[C:30]=1[C:23]1[C:22]([CH2:21][O:20][C:17]2[CH:18]=[CH:19][C:14]([C:10]3[CH:9]=[C:8]4[C:13]([C:5]([C:3]([OH:4])=[O:2])=[C:6]([CH3:42])[N:7]4[CH:39]([CH3:40])[CH3:41])=[CH:12][CH:11]=3)=[C:15]([CH3:38])[CH:16]=2)=[C:26]([CH:27]([CH3:29])[CH3:28])[O:25][N:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67272198HCID 67272198, compound

Product 1

HCID 58088352HCID 58088352, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-{4-[3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-2-methyl-phenyl}-1-isopropyl-2-methyl-1H-indole-3-carboxylic acid methyl ester (239 mg, 0.390 mmol), sodium hydroxide (5 M, 0.5 mL) and methanol (1 mL) is heated in a microwave reactor utilizing the lowest power setting at 125° C. for 20 minutes. The mixture is acidified with 1 N HCl and extracted with ether. The ether layers are washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue is purified on a via radial chromatography (2 mm plate, 3% MeOH—CH2Cl2) to yield the title compound (59 mg, 25%) as a white solid. ES/MS m/e 592.8 (M+1)

Workup

  1. temperatureis heated in a microwave reactor
  2. customat 125° C.
  3. customfor 20 minutes
  4. extractionextracted with ether
  5. washThe ether layers are washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified on a via radial chromatography (2 mm plate, 3% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-6769333604be4a5b88ebca923a177a58
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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