HCID 54755922, compound → 3-({[1-(4-Hydroxy-4-thiazol-2-yl-cyclohexyl)-azetidin-3-ylcarbamoyl]-methyl}-amino)-5-trifluoromethyl-indazole-1-carboxylic acid amide

HRID 2089217Notes

Reaction equation

HRID 2089217 reaction equation
C([NH:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=2)[C:10]([NH:21][CH2:22][C:23](=[O:41])[NH:24][CH:25]2[CH2:28][N:27]([CH:29]3[CH2:34][CH2:33][C:32]([OH:40])([C:35]4[S:36][CH:37]=[CH:38][N:39]=4)[CH2:31][CH2:30]3)[CH2:26]2)=[N:9]1)=[O:7])(C)(C)C>C(O)(C(F)(F)F)=O>[OH:40][C:32]1([C:35]2[S:36][CH:37]=[CH:38][N:39]=2)[CH2:31][CH2:30][CH:29]([N:27]2[CH2:26][CH:25]([NH:24][C:23]([CH2:22][NH:21][C:10]3[C:11]4[C:16](=[CH:15][CH:14]=[C:13]([C:17]([F:19])([F:20])[F:18])[CH:12]=4)[N:8]([C:6]([NH2:5])=[O:7])[N:9]=3)=[O:41])[CH2:28]2)[CH2:34][CH2:33]1

Participants

3

Reactant 1

HCID 54755922HCID 54755922, compound

Product 1

HCID 547556813-({[1-(4-Hydroxy-4-thiazol-2-yl-cyclohexyl)-azetidin-3-ylcarbamoyl]-methyl}-amino)-5-trifluoromethyl-indazole-1-carboxylic acid amideYield 27%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

3-({[1-(4-Hydroxy-4-thiazol-2-yl-cyclohexyl)-azetidin-3-ylcarbamoyl]-methyl}-amino)-5-trifluoromethyl-indazole-1-carboxylic acid tert-butylamide (as prepared in Example 80, 150 mg, 0.25 mmol) in TFA (2 mL) in a sealed tube was heated at 80° C. for 6 hours. The TFA was removed, and the residue was partitioned between DCM and saturated NaHCO3. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude material, purified by silica gel column (DCM: 7 N NH3 in MeOH 9:1) to afford the title compound as white solid (36 mg, 27%).

Workup

  1. customThe TFA was removed
  2. customthe residue was partitioned between DCM and saturated NaHCO3
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude material
  8. custompurified by silica gel column (DCM: 7 N NH3 in MeOH 9:1)

Sources & evidence

ORD record
ord-5bac27ef093441d8afeab6769cfb08d1
Source dataset
uspto-grants-2013_05
Patent number
US08436023B2

Reaction notes

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