Sodium Methoxide → 7-[3-(Acetylamino)-1-piperidinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

HRID 729065노트

반응식

HRID 729065 반응식
[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[C:20](F)=[C:19]3[C:14]([C:15](=[O:28])[C:16]([C:25]([OH:27])=[O:26])=[CH:17][N:18]3[CH:22]3[CH2:24][CH2:23]3)=[CH:13][C:12]=2[F:29])[CH2:6]1)(=[O:3])[CH3:2].[CH3:30][O-:31].[Na+]>CN(C)C=O>[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[C:20]([O:31][CH3:30])=[C:19]3[C:14]([C:15](=[O:28])[C:16]([C:25]([OH:27])=[O:26])=[CH:17][N:18]3[CH:22]3[CH2:23][CH2:24]3)=[CH:13][C:12]=2[F:29])[CH2:6]1)(=[O:3])[CH3:2]

참가 물질

4

반응물 2

HCID 10942334Sodium MethoxideHCID 15670689HCID 15670689, 화합물

생성물 1

HCID 156706907-[3-(Acetylamino)-1-piperidinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 7-(3-acetamidopiperidin-1-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (4.05 g), sodium methoxide (2.16 g) and N,N-dimethylformamide (120 ml) was stirred for 2 hours at 100°-140° C. The reaction mixture was concentrated in vacuumand water was added to the residue. The mixture was neutralized with 1N hydrochloric acid and the neutralized mixture was then concentrated in vacuum. Purification of the concentrated mixture by silica gel column chromatography (chloroform-methanol) gave 7-(3-acetamidopiperidin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid. m.p. 248°-250° C.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuumand water
  2. additionwas added to the residue
  3. concentrationthe neutralized mixture was then concentrated in vacuum
  4. customPurification of the concentrated mixture by silica gel column chromatography (chloroform-methanol)

출처 및 근거

ORD 기록
ord-75f80f9023b04b808b9b48e9a97f7d3e
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05051509

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