Hydrochloric Acid → HCID 68648325, compound

HRID 1162597Notes

Reaction equation

HRID 1162597 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:14]2[S:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=3)[N:18]=2)[N:6]=1)=[O:4].[Li+].[OH-].[ClH:30]>[Cl-].[Na+].O>[ClH:30].[CH:25]([C:22]1[CH:23]=[CH:24][C:19]([C:17]2[N:18]=[C:14]([N:7]3[C:8]4[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:5]([C:3]([OH:4])=[O:2])=[N:6]3)[S:15][CH:16]=2)=[CH:20][CH:21]=1)([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68647827HCID 68647827, compound

Product 1

HCID 68648325HCID 68648325, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To the 1-[4-(4-isopropyl-phenyl)-thiazol-2-yl]-1H-indazole-3-carboxylic acid methyl ester (150 mg, 0.22 mmol) was added LiOH (5 mL; 2N LiOH-MeOH-THF=1:1:4) and stirred at room temperature for 4 h before acidifying with 1N HCl. Brine was added and the aqueous was extracted with DCM (3×15 ml). Combined extracts were dried over Na2SO4, concentrated and purified on silica gel column to provide 1-[4-(4-Isopropyl-phenyl)-thiazol-2-yl]-1H-indazole-3-carboxylic acid hydrochloride salt (48 mg). LCMS m/z: 365 (M+1)+.

Workup

  1. extractionthe aqueous was extracted with DCM (3×15 ml)
  2. dry with materialCombined extracts were dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified on silica gel column

Sources & evidence

ORD record
ord-13ece7f572214aabba4123391e9063c6
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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