Sodium Hydroxide → N-[6-(4-Hydroxyphenyl)-1H-indazol-4-yl]cyclohexanecarboxamide

HRID 1695769Notes

Reaction equation

HRID 1695769 reaction equation
CCN(C(C)C)C(C)C.[CH:10]1([C:16](Cl)=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.O1CCCCC1[N:25]1[CH:33]=[C:32]2[C:27]([CH:28]=[C:29]([C:35]3[CH:40]=[CH:39][C:38]([O:41]C4CCCCO4)=[CH:37][CH:36]=3)[CH:30]=[C:31]2[NH2:34])=[N:26]1.[OH-].[Na+]>C(Cl)Cl>[OH:41][C:38]1[CH:37]=[CH:36][C:35]([C:29]2[CH:28]=[C:27]3[C:32]([CH:33]=[N:25][NH:26]3)=[C:31]([NH:34][C:16]([CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)=[O:17])[CH:30]=2)=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 75938Cyclohexanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 582558372-(Tetrahydro-2H-pyran-2-yl)-6-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]-2H-indazol-4-amine

Product 1

HCID 135927900N-[6-(4-Hydroxyphenyl)-1H-indazol-4-yl]cyclohexanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIPEA (82 mg, 0.635 mmol) and cyclohexanecarbonyl chloride (37 mg, 0.254 mmol) were added to 2-(tetrahydro-2H-pyran-2-yl)-6-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]-2H-indazol-4-amine (50 mg, 0.127 mmol) in DCM (1 ml) and the reaction was stirred for 1 h. 2 M Sodium hydroxide (aq) (2 ml) was added and the reaction stirred for 1 h. The organic layer was passed through a hydrophobic frit and the aqueous layer was extracted with DCM. The organic layers were combined and the solvent removed under a stream of nitrogen. The residue was dissolved in MeOH (2 ml), 4 M HCl in 1,4-dioxane (2 ml) was added and the reaction was stirred at RT for 1 h. The solvent was removed under a stream of nitrogen. The residue was purified by MDAP using the following method:

Workup

  1. stirringthe reaction stirred for 1 h
  2. extractionthe aqueous layer was extracted with DCM
  3. customthe solvent removed under a stream of nitrogen
  4. dissolutionThe residue was dissolved in MeOH (2 ml)
  5. addition4 M HCl in 1,4-dioxane (2 ml) was added
  6. stirringthe reaction was stirred at RT for 1 h
  7. customThe solvent was removed under a stream of nitrogen
  8. customThe residue was purified by MDAP

Sources & evidence

ORD record
ord-57a9b06ae4a94a62a127b39c29af9388
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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