Sodium hydride → N-[2-(4-Chloro-phenyl)-2H-indazol-3-yl]-2,N-dicyclohexyl-acetamide

HRID 1690584Notes

Reaction equation

HRID 1690584 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]([NH:19][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[CH:16]3)=[N:11]2)=[CH:6][CH:5]=1.[CH:26]1([CH2:32][C:33](Cl)=[O:34])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C(OC(C)=O)(C)C.[Cl-].[Na+].O>CN(C=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]([N:19]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:33](=[O:34])[CH2:32][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[CH:16]3)=[N:11]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 2757989Cyclohexylacetyl chlorideHCID 66905444[2-(4-Chloro-phenyl)-2H-indazol-3-yl]cyclohexyl-amineHCID 131729614iPrOAc brine

Product 1

HCID 45111483N-[2-(4-Chloro-phenyl)-2H-indazol-3-yl]-2,N-dicyclohexyl-acetamideYield 6.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

To an ice cold suspension of NaH (13 mg, 340 μmol) in DMF (5 ml) under an argon atmosphere was added a solution of [2-(4-chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-amine (100 mg, 310 μmol; example 11.1) in DMF (1 ml) within 10 min. The suspension was stirred for 1 h at 0° C. A solution of cyclohexyl-acetyl chloride (50 μl, 340 μmol; [23860-35-7]) in DMF (1 ml) was added within 5 min. The reaction mixture was stirred for 14 h at ambient temperature, poured onto ice water/brine 1/1 and extracted two times with iPrOAc. The combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, iPrOAc/heptane) to give the title compound (8 mg, 20 μmol; 6%) as yellow oil. MS: m/e=450.0 [M+H+].

Workup

  1. stirringThe reaction mixture was stirred for 14 h at ambient temperature
  2. extractionextracted two times with iPrOAc
  3. washThe combined extracts were washed with ice water/brine 1/1
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography (silica gel, iPrOAc/heptane)

Sources & evidence

ORD record
ord-b65253e19f4445f0837e4d0e958041a3
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

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