Triethylamine → Ethyl 7-[2(acetamidomethyl)-4-thiazolyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

HRID 978511Notes

Reaction equation

HRID 978511 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:22])[C:10]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][N:12]2[CH2:15][CH3:16])=[CH:7][C:6]=1[F:23])=O.[C:24]([NH:27][CH2:28][C:29]([NH2:31])=[S:30])(=[O:26])[CH3:25].C(N(CC)CC)C>CN(C)C=O>[C:24]([NH:27][CH2:28][C:29]1[S:30][CH:2]=[C:3]([C:5]2[CH:14]=[C:13]3[C:8]([C:9](=[O:22])[C:10]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][N:12]3[CH2:15][CH3:16])=[CH:7][C:6]=2[F:23])[N:31]=1)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4435531N-(2-amino-2-thioxoethyl)acetamideHCID 13853634Ethyl 7-bromoacetyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3quinolinecarboxylate

Product 1

HCID 13772764Ethyl 7-[2(acetamidomethyl)-4-thiazolyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylateYield 57.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 0.59 g (1.54 mmol) ethyl 7-bromoacetyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate in 4 ml N,N-dimethylformamide was treated with 0.22 g (1.67 mmol) acetamidothioacetamide [prepared according to J. Am. Chem. Soc. 51, 1817 (1929)]. After stirring three hours the mixture was treated with 0.22 ml (1.58 mmol) triethylamine, stirred one hour more and poured into 40 ml ice water. The precipitate was filtered, washed with water and dried to afford 0.45 g crude solid. Chromatography on a column of 20 g silica gel with chloroform-methanol (9:1) and crystallization from ethanol gave 0.37 g ethyl 7-[2(acetamidomethyl)-4-thiazolyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, mp 230°-233° C. (dec).

Workup

  1. stirringstirred one hour more
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried
  5. customto afford 0.45 g crude solid
  6. customChromatography on a column of 20 g silica gel with chloroform-methanol (9:1) and crystallization from ethanol

Sources & evidence

ORD record
ord-065dc7fea5334e23bc54b946bfdbdc1d
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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