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

HRID 978511ノート

反応式

HRID 978511 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-065dc7fea5334e23bc54b946bfdbdc1d
出典データセット
uspto-grants-1987_05
特許番号
US04665079

反応ノート

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