1,1-Dichloroethane → HCID 12988030, compound

HRID 1582982Notes

Reaction equation

HRID 1582982 reaction equation
ClC(Cl)C.[NH2:5][CH2:6][CH2:7][CH2:8][C:9]1[C:10](=[O:29])[N:11]([CH2:27][CH3:28])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1)=[CH:16][CH:15]=[C:14]([CH3:26])[N:13]=2.[CH3:30][S:31](Cl)(=[O:33])=[O:32].C(N(CC)CC)C>C(OCC)(=O)C>[Cl:25][C:21]1[CH:20]=[C:19]([C:18]2[C:17]3[C:12](=[N:13][C:14]([CH3:26])=[CH:15][CH:16]=3)[N:11]([CH2:27][CH3:28])[C:10](=[O:29])[C:9]=2[CH2:8][CH2:7][CH2:6][NH:5][S:31]([CH3:30])(=[O:33])=[O:32])[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 63651,1-DichloroethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22716704HCID 22716704, compound

Product 1

HCID 12988030HCID 12988030, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 10 ml dichloroethane solution containing 630 mg of 3-(3-aminopropyl)-4-(3-chlorophenyl)-l-ethyl-7-methyl-1,8-naphthyridin-2(1H)-one were added 243 mg of methanesulfonyl chloride and 0.30 ml of triethylamine under ice cooling, followed by stirring for 1 hour with warming to room temperature. The reaction mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate aqueous solution and saturated brine. The solvent was evaporated from the organic layer and the resulting residue was purified by a silica gel column chromatography (hexane-ethyl acetate) and then recrystallized from ethanol-water to obtain 204 mg of N-{3-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propyl}methanesulfonamide as colorless crystals.

Workup

  1. washwashed with saturated sodium bicarbonate aqueous solution and saturated brine
  2. customThe solvent was evaporated from the organic layer
  3. customthe resulting residue was purified by a silica gel column chromatography (hexane-ethyl acetate)
  4. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-78cdc012a9b446a897ae14f068adffd5
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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