Sodium Bicarbonate → N-(4-(4-(Ethyl(6-fluoro-6-methylheptyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide

HRID 1654303Notes

Reaction equation

HRID 1654303 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=1)[OH:8])[CH3:2].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([F:29])([CH3:28])[CH3:27].C(=O)(O)[O-].[Na+]>C(#N)C>[CH2:1]([N:3]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([F:29])([CH3:28])[CH3:27])[CH2:4][CH2:5][CH2:6][CH:7]([C:9]1[CH:10]=[CH:11][C:12]([NH:15][S:16]([CH3:19])(=[O:17])=[O:18])=[CH:13][CH:14]=1)[OH:8])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10750976Heptane, 1-bromo-6-fluoro-6-methyl-HCID 10779588N-(4-(4-(ethylamino)-1-hydroxybutyl)phenyl)methanesulfonamide

Product 1

HCID 9823219N-(4-(4-(Ethyl(6-fluoro-6-methylheptyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(Procedure B) A stirred mixture of the product from Example 7, Step II, (0.37 g, 0.00128 mol), the product from Step III above (0.298 g, 0.0141 mol), sodium bicarbonate (0.21 g, 0.0026 mol) and acetonitrile (11 ml) was refluxed for 5 hours and kept at ambient temperature for 18 hours. It was filtered and the solid was washed with acetonitrile. The filtrate was concentrated and the residue was chromatographed on silica gel with 10% MeOH--CH2Cl2 to give 0.332 g of the titled product, a compound of Formula I'. The mass spectrum had m/z 416 (M+).

Workup

  1. filtrationIt was filtered
  2. washthe solid was washed with acetonitrile
  3. concentrationThe filtrate was concentrated
  4. customthe residue was chromatographed on silica gel with 10% MeOH

Sources & evidence

ORD record
ord-1fc28eef807a4c6295390210a500cfaa
Source dataset
uspto-grants-1995_04
Patent number
US05405997

Reaction notes

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