Sodium hydride → 5-Chloro-6-((4-(cyclopropyl(oxetan-3-yl)amino)cyclohexyl)methoxy)pyridine-3-sulfonamide

HRID 1036022Notes

Reaction equation

HRID 1036022 reaction equation
[CH:1]1([N:4]([CH:13]2[CH2:16][O:15][CH2:14]2)[CH:5]2[CH2:10][CH2:9][CH:8]([CH2:11][OH:12])[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[H-].[Na+].[Cl:19][C:20]1[CH:21]=[C:22]([S:27]([NH2:30])(=[O:29])=[O:28])[CH:23]=[N:24][C:25]=1Cl.[NH4+].[Cl-]>CN(C)C=O>[Cl:19][C:20]1[CH:21]=[C:22]([S:27]([NH2:30])(=[O:29])=[O:28])[CH:23]=[N:24][C:25]=1[O:12][CH2:11][CH:8]1[CH2:7][CH2:6][CH:5]([N:4]([CH:1]2[CH2:2][CH2:3]2)[CH:13]2[CH2:16][O:15][CH2:14]2)[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 47309215,6-Dichloropyridine-3-sulfonamideHCID 67126731[4-[Cyclopropyl(oxetan-3-yl)amino]cyclohexyl]methanol

Product 1

HCID 671267985-Chloro-6-((4-(cyclopropyl(oxetan-3-yl)amino)cyclohexyl)methoxy)pyridine-3-sulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of EXAMPLE 329C (706 mg) in N,N-dimethylformamide (6 mL) was added NaH (60% in mineral oil, 300 mg). The mixture was stirred for 30 minutes, and then 5,6-dichloropyridine-3-sulfonamide (706 mg) was added. The mixture was stirred overnight. The mixture was poured over aqueous NH4Cl and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with water, brine and dried over Na2SO4. After filtration and evaporation of the solvent the residue was loaded on a silica gel cartridge and eluted with 5 to 10% 7N NH3 in methanol in dichloromethane to provide the title compound.

Workup

  1. stirringThe mixture was stirred overnight
  2. extractionextracted with ethyl acetate (3×200 mL)
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and evaporation of the solvent the residue
  6. washeluted with 5 to 10% 7N NH3 in methanol in dichloromethane

Sources & evidence

ORD record
ord-169c06902316441f98489248237c2d8e
Source dataset
uspto-grants-2013_10
Patent number
US08546399B2

Reaction notes

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