Sodium Bicarbonate → 6-fluoro-1-methyl-4-[2-[4-(thieno[3,2-c]pyridine-4-yl)-1-piperazinyl]ethyl]-2(1H)-quinolone hydrochloride

HRID 619117Notes

Reaction equation

HRID 619117 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:14])[CH:12]=2)[N:7]([CH3:15])[C:6](=[O:16])[CH:5]=1.[N:17]1([C:23]2[C:28]3[CH:29]=[CH:30][S:31][C:27]=3[CH:26]=[CH:25][N:24]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(=O)([O-])O.[Na+]>C(#N)C>[ClH:1].[F:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:15])[C:6](=[O:16])[CH:5]=[C:4]2[CH2:3][CH2:2][N:20]1[CH2:21][CH2:22][N:17]([C:23]2[C:28]3[CH:29]=[CH:30][S:31][C:27]=3[CH:26]=[CH:25][N:24]=2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 109660274-(Piperazin-1-yl)thieno[3,2-c]pyridineHCID 218460434-(2-chloroethyl)-6-fluoro-1-methyl-2(1H)-quinolone

Product 1

HCID 218460396-fluoro-1-methyl-4-[2-[4-(thieno[3,2-c]pyridine-4-yl)-1-piperazinyl]ethyl]-2(1H)-quinolone hydrochlorideYield 27%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
57.5 °C

Procedure

1.4 g (5.8 mmol) of 4-(2-chloroethyl)-6-fluoro-1-methyl-2(1H)-quinolone are added to a mixture of 1.3 g (5.9 mmol) of 4-(1-piperazinyl)thieno[3,2-c]pyridine and 0.50 g (5.95 mmol) of sodium hydrogen carbonate in 20 ml of acetonitrile, and the reaction medium is heated to 55-60° C. for 18 hours. The solvent is evaporated off and the residue is taken up in 100 ml of dichloromethane. It is washed with saturated aqueous sodium bicarbonate solution and then with water. The organic phase is dried over sodium sulphate and filtered and the filtrate is condensed. The crude product is purified by flash chromatography on silica, eluting with a methanol/dichloromethane (5:95) mixture containing traces of aqueous ammonia. 0.70 g of the expected product is obtained in base form.

Workup

  1. customThe solvent is evaporated off
  2. washIt is washed with saturated aqueous sodium bicarbonate solution
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. filtrationfiltered
  5. customcondensed
  6. customThe crude product is purified by flash chromatography on silica
  7. washeluting with a methanol/dichloromethane (5:95) mixture
  8. additioncontaining traces of aqueous ammonia

Sources & evidence

ORD record
ord-0176029c30724412b685e2b0d7b42484
Source dataset
uspto-grants-1999_09
Patent number
US05958924

Reaction notes

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