Thiomorpholine → HCID 10668222, compound

HRID 568823Notes

Reaction equation

HRID 568823 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:23])[C:7]([C:20]([OH:22])=[O:21])=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=2)=[CH:4][C:3]=1[F:24].ClC1[N:27]([C:41]2[CH:46]=CC(F)=CC=2)[C:28]2C(C(=O)C=1C(O)=O)=CC(F)=C[CH:29]=2.[NH:48]1CCSCC1>CN1CCCC1=O>[C:18]([C:15]1[CH:14]=[CH:13][C:12]([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:24])=[C:2]([N:48]4[CH2:46][CH2:41][NH:27][CH2:28][CH2:29]4)[CH:11]=3)[C:6](=[O:23])[C:7]([C:20]([OH:22])=[O:21])=[CH:8]2)=[CH:17][CH:16]=1)#[N:19]

Participants

5

Reactant 3

HCID 67164ThiomorpholineHCID 19783732HCID 19783732, compoundHCID 20149300HCID 20149300, compound

Product 1

HCID 10668222HCID 10668222, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of 3.36 g of 7 chloro-1-p-fluoro-phenyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (the product of Example 4(b)) in 35 ml of 1-methyl-2-pyrrolidinone at 115° C. is added 4.13 g of thiomorpholine. After stirring at 115° C. for 20 hours, the solvent is removed by reduced pressure to dryness. Methanol is added to the residue and the resulting mixture is filtered and washed with ethylacetate and then washed with water. The solid is dried, yielding 2.51 g 1-p-fluorophenyl-6-fluoro-1,4-dihydro-4-oxo-7-thiomorpholino-quinoline-3-carboxylic acid (9) ##STR36## R=p-fluorophenyl) in 62% yield.

Workup

  1. customthe solvent is removed by reduced pressure to dryness
  2. additionMethanol is added to the residue
  3. filtrationthe resulting mixture is filtered
  4. washwashed with ethylacetate
  5. washwashed with water
  6. customThe solid is dried

Sources & evidence

ORD record
ord-2acc54ceb1b845af845fec96aaba23d9
Source dataset
uspto-grants-1988_03
Patent number
US04730000

Reaction notes

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