Dimethylformamide → 1,4-Dihydro-4-oxo-6-[[(5-oxo-2-pyrrolidinyl)carbonyl]-amino]-3-quinolinecarboxylic acid

HRID 851001

반응식

HRID 851001 반응식
[O:1]=[C:2]1[NH:6][C@H:5]([C:7]([OH:9])=O)[CH2:4][CH2:3]1.CN(C)C=O.[NH2:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]([C:26]([OH:28])=[O:27])[C:19]2=[O:29].C(N(CC)CC)C.Cl[Si](C)(C)C>ClCCl>[O:29]=[C:19]1[C:18]2[C:23](=[CH:24][CH:25]=[C:16]([NH:15][C:7]([CH:5]3[CH2:4][CH2:3][C:2](=[O:1])[NH:6]3)=[O:9])[CH:17]=2)[NH:22][CH:21]=[C:20]1[C:26]([OH:28])=[O:27]

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 6397ChlorotrimethylsilaneHCID 7405L-Pyroglutamic AcidHCID 8471TriethylamineHCID 32812016-Amino-4-hydroxyquinoline-3-carboxylic acid

생성물 1

HCID 205034361,4-Dihydro-4-oxo-6-[[(5-oxo-2-pyrrolidinyl)carbonyl]-amino]-3-quinolinecarboxylic acid수율 57.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A mixture of 1.94 g (15 mmol) of 5-oxo-L-proline, 1.1 ml (15 mol) dimethylformamide, and 30 ml of dichloromethane is stirred 0°-5° for 1 hour. A mixture of 2.04 g (10 mmol) of 6-amino-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, [J. Pharm. Sci., 11, 1051 (1963)] 4.2 ml (30 mmol) of triethylamine, 3.8 ml (30 mmol) of chlorotrimethylsilane, and 75 ml of dichloromethane is stirred at room temperature for 40 minutes and then is cooled at 0°. The cold acid chloride solution is added to the cold silylated quinoline and is stirred at 5° for 4 hours and overnight at room temperature. The reaction mixture is evaporated and the residue is treated with water to give 1.81 g of 1,4-dihydro-4-oxo-6-[[(5-oxo-2-pyrrolidinyl)carbonyl]-amino]-3-quinolinecarboxylic acid.

후처리

  1. stirringis stirred at room temperature for 40 minutes
  2. temperatureis cooled at 0°
  3. stirringis stirred at 5° for 4 hours and overnight at room temperature
  4. customThe reaction mixture is evaporated
  5. additionthe residue is treated with water

출처 및 근거

ORD 기록
ord-580ae60b76084f6b95519a1664839764
출처 데이터셋
uspto-grants-1983_05
특허 번호
US04382089

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