Acetic Acid → 7-(2-Aminopyrimidin-4-yl)-1-ethyl-6-fluoro-4-oxo-quinoline-3-carboxylic acid

HRID 622504Notes

Reaction equation

HRID 622504 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([C:18]([CH:20]=[CH:21]N(C)C)=O)=[C:12]([F:17])[CH:13]=2)[N:8]([CH2:25][CH3:26])[CH:7]=1)=[O:5])C.Cl.[NH2:28][C:29]([NH2:31])=[NH:30].CC(C)([O-])C.[K+].C(O)(=O)C>C(O)(C)(C)C>[NH2:30][C:29]1[N:31]=[C:18]([C:11]2[CH:10]=[C:9]3[C:14]([C:15](=[O:16])[C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]3[CH2:25][CH3:26])=[CH:13][C:12]=2[F:17])[CH:20]=[CH:21][N:28]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5742Guanidine HydrochlorideHCID 23665647Potassium tert-butoxideHCID 540574497-(2'-Dimethylaminoethenyl)carbonyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester

Product 1

HCID 4614397-(2-Aminopyrimidin-4-yl)-1-ethyl-6-fluoro-4-oxo-quinoline-3-carboxylic acidYield 35.9%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

To 900 mg (2.5 mmol) of the 7-(2'-dimethylaminoethenyl)carbonyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester in 15 ml of t-butanol at 50° C. was added 580 mg (2.5 eq) of guanidine hydrochloride that had been previously treated with 1.35 g (5 eq) of potassium t-butoxide at 50° C. in t-butanol for 30 minutes. The final mixture was stirred for 24 hours at 60° C. It was poured into 8% aqueous acetic acid and extracted into chloroform. The chloroform was extracted three times with water. The chloroform was dried magnesium sulfate and concentrated. The residue was purified by column chromatography and gave 295 mg of 7-(2-amino-4-pyrimidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, mp 245°-247° C.

Workup

  1. extractionextracted into chloroform
  2. extractionThe chloroform was extracted three times with water
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-78bbe877ed1148e9903fa8147f2c6f56
Source dataset
uspto-grants-1988_09
Patent number
US04771054

Reaction notes

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