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Water → (RS)-7-Fluoro-8-[3-(2-furyl)-1-piperazinyl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

HRID 344914
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인쇄 미리보기

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HRID 344914 반응식
C([O:3][C:4]([C:6]1[C:7](=[O:33])[C:8]2[CH:9]=[C:10]3[CH:20]=[C:19]([F:21])[C:18]([N:22]4[CH2:27][CH2:26][NH:25][CH:24]([C:28]5[O:29][CH:30]=[CH:31][CH:32]=5)[CH2:23]4)=[CH:17][C:11]3=[N:12][C:13]=2[N:14]([CH3:16])[CH:15]=1)=[O:5])C.CS(O)(=O)=O.O>[OH-].[K+].C(O)C>[F:21][C:19]1[C:18]([N:22]2[CH2:27][CH2:26][NH:25][CH:24]([C:28]3[O:29][CH:30]=[CH:31][CH:32]=3)[CH2:23]2)=[CH:17][C:11]2=[N:12][C:13]3[N:14]([CH3:16])[CH:15]=[C:6]([C:4]([OH:5])=[O:3])[C:7](=[O:33])[C:8]=3[CH:9]=[C:10]2[CH:20]=1
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참가 물질

6

반응물 3

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 53959778(RS)-3-ethoxycarbonyl-7-fluoro-8-[3-(2-furyl)-1-piperazinyl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

생성물 1

HCID 53954693(RS)-7-Fluoro-8-[3-(2-furyl)-1-piperazinyl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid수율 46.8%

시약·촉매·용매 2

HCID 702
Ethanol
용매
HCID 14797Potassium Hydroxide용매

반응 조건

온도
80 °C

실험 절차

A suspension of (RS)-3-ethoxycarbonyl-7-fluoro-8-[3-(2-furyl)-1-piperazinyl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (1.3 g) in 0.5 N aqueous potassium hydroxide (12 cc) and ethanol (12 cc) is heated for 1 hour to a temperature in the region of 80° C. and then treated at the same temperature with an N aqueous solution (6 cc) of methanesulphonic acid. After cooling to approximately 20° C., the insoluble water is drained, washed with water (3×10 cc), ethanol (3×10 cc) and ethyl ether (3×10 cc) and recrystallized in a mixture of ethanol (13 cc) and dimethylformamide (27 cc). (RS)-7-Fluoro-8-[3-(2-furyl)-1-piperazinyl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid (0.570 g) obtained in the form of a yellow solid, m.p. 258°-260° C.

후처리

  1. temperatureAfter cooling to approximately 20° C.
  2. washwashed with water (3×10 cc), ethanol (3×10 cc) and ethyl ether (3×10 cc)
  3. customrecrystallized in a mixture of ethanol (13 cc) and dimethylformamide (27 cc)

출처 및 근거

ORD 기록
ord-32535ec13def4d8d8ba3c767a1a6fd97
출처 데이터셋
uspto-grants-1991_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05053509

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