Sodium hydride → HCID 45111485, compound

HRID 1690586Notes

Reaction equation

HRID 1690586 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]C[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.[N:26]([CH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1)=[C:27]=[O:28]>CN(C=O)C.[Cl-].[Na+].O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:18]([N:19]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:21]3)[C:27]([NH:26][CH:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[O:28])=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[CH:16]3)=[N:11]2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 643500Cyclopentyl IsocyanateHCID 66905444[2-(4-Chloro-phenyl)-2H-indazol-3-yl]cyclohexyl-amine

Product 1

HCID 45111485HCID 45111485, compoundYield 30.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

To an ice cold suspension of NaH (6 mg, 160 umol) in DMF (2.5 ml) under an argon atmosphere was added a solution of [2-(4-chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-amine (50 mg, 153 umol; example 11.1) in DMF (1 ml) within 10 min. The suspension was stirred for 1 h at 0° C. A solution of isocyanato-cyclopentane (34 mg, 306 umol; [4747-71-1]) in DMF (0.5 ml) was added within 5 min. The reaction mixture was stirred for 1 h at ambient temperature, poured onto ice water/1 N aqueous HCl solution/brine 1/1/1 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 (20 mg, 47 umol; 21%) as yellow foam. MS: m/e=423.1 [M+H+].

Workup

  1. stirringThe reaction mixture was stirred for 1 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-48e1f5b1306849f995546079d82c0b0b
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

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