2-Aminothiazole → HCID 11046433, compound

HRID 2290520Notes

Reaction equation

HRID 2290520 reaction equation
F[C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([F:10])=[CH:4][C:3]=1[C:11](=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C(OC(O[CH2:27][CH3:28])OCC)C.C(OC(=O)C)(=O)C.[NH2:36][C:37]1[S:38]C=[CH:40][N:41]=1>C(O)(C)C>[F:10][C:5]1[CH:4]=[C:3]2[C:2](=[C:7]([F:8])[C:6]=1[F:9])[N:41]([C:37]1[S:38][CH:27]=[CH:28][N:36]=1)[CH:40]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11]2=[O:18]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 600916Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoate

Product 1

HCID 11046433HCID 11046433, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 3.0 g (11.33 mmol) of 2,3,4,5-tetrafluoro-β-oxo-benzeneproprionic acid, ethyl ester was added 2.49 g of triethylorthoformate and 2.76 g of acetic anhydride. The mixture was refluxed for two hours and concentrated to dryness under high vacuum at 80° C. The residual oil was treated with 1.32 g (1.2 equivalents) of 2-aminothiazole suspended in 70 ml of isopropanol. At 70° C., 1.6 g (1.0 equivalent) of 1,8-diazobicyclo[5.4.0]undec-7-ene was added. After 18 hours, the mixture was cooled and filtered to give 2.73 g of the 6,8,7-trifluoro-1,4-dihydro-4-oxo-1-(2-thiazolyl)-3-quinolinecarboxylic acid, ethyl ester, mp 172°-174° C. This material was dissolved in 100 ml of hot acetic acid and 50 ml of 2N hydrochloric acid and was heated at 100° C. for 2.5 hours. The mixture was cooled, partially concentrated, and filtered to give 1.81 g of 6,7,8-trifluoro-1,4-dihydro-4-oxo-1-(2-thiazolyl)-3-quinolinecarboxylic acid, mp 198.5°-200° C.

Workup

  1. temperatureThe mixture was refluxed for two hours
  2. concentrationconcentrated to dryness under high vacuum at 80° C
  3. temperaturethe mixture was cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-6a187780d6414f0293b2333b09906aa4
Source dataset
uspto-grants-1986_10
Patent number
US04617308

Reaction notes

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