Water → HCID 56661559, compound

HRID 2089176Notes

Reaction equation

HRID 2089176 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([N:12]2[CH2:15][CH:14]([NH:16][C:17](=[O:34])[CH2:18][NH:19][C:20]3[C:28]4[C:23](=[CH:24][CH:25]=[C:26]([C:29]([F:32])([F:31])[F:30])[CH:27]=4)[N:22]([CH3:33])[N:21]=3)[CH2:13]2)[CH2:8][CH2:7]1)=[O:5])C.O.O.[OH-].[Li+]>C1COCC1.CO>[CH3:33][N:22]1[C:23]2[C:28](=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[C:20]([NH:19][CH2:18][C:17]([NH:16][CH:14]2[CH2:13][N:12]([CH:9]3[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]3)[CH2:15]2)=[O:34])=[N:21]1

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 566719254-{3-[2-(1-Methyl-5-trifluoromethyl-1H-indazol-3-ylamino)-acetylamino]-azetidin-1-yl}-cyclohexane carboxylic acid ethyl ester

Product 1

HCID 56661559HCID 56661559, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-{3-[2-(1-Methyl-5-trifluoromethyl-1H-indazol-3-ylamino)-acetylamino]-azetidin-1-yl}-cyclohexane carboxylic acid ethyl ester (from Example 32, 350 mg, 0.773 mmol) in THF (2 mL), MeOH (2 mL) and distilled water (2 mL) was treated with lithium hydroxide monohydrate (87 mg, 1.93 mmol) at room temperature for 1 hour. The reaction mixture was acidified to pH=5 and extracted with DCM:IPA (3:1) solvent three times. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the title compound as colorless solid.

Workup

  1. extractionextracted with DCM:IPA (3:1) solvent three times
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-40a90e80670f490083cd8ad9a758354e
Source dataset
uspto-grants-2013_05
Patent number
US08436023B2

Reaction notes

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