Sodium hydride → HCID 45111484, compound

HRID 1690585Notes

Reaction equation

HRID 1690585 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.Cl[C:27]([O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)=[O:28].C(OC(C)=O)(C)C.[Cl-].[Na+].O>CN(C=O)C>[CH:30]1([O:29][C:27](=[O:28])[N:19]([C:18]2[N:10]([C:7]3[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=3)[N:11]=[C:12]3[C:17]=2[CH:16]=[CH:15][CH:14]=[CH:13]3)[CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 83262Carbonochloridic acid, cyclohexyl esterHCID 66905444[2-(4-Chloro-phenyl)-2H-indazol-3-yl]cyclohexyl-amineHCID 131729614iPrOAc brine

Product 1

HCID 45111484HCID 45111484, compoundYield 4.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To an ice cold suspension of NaH (6 mg, 160 umol) in DMF (3 ml) under an argon atmosphere was added a solution of [2-(4-chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-amine (50 mg, 153 μmol; example 11.1) in DMF (1 ml) within 10 min. The suspension was stirred for 1 h at ambient temperature. A solution of cyclohexyl chloroformate (33 mg, 203 μmol; [13248-54-9]) 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 brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by preparative thin layer chromatography (silica gel, iPrOAc/heptane) to give the title compound (3 mg, 7 μmol; 3%) as brown solid. MS: m/e=452.4 [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 brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by preparative thin layer chromatography (silica gel, iPrOAc/heptane)

Sources & evidence

ORD record
ord-3940035211a6447ba835df62e594c351
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

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