Triethylamine → 7-(trans-3-Amino-4-methoxy-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride

HRID 358866노트

반응식

HRID 358866 반응식
C[O-].[Na+].[ClH:4].Cl.[NH2:6][C@H:7]1[C@H:11]([O:12][CH3:13])[CH2:10][NH:9][CH2:8]1.[CH:14]1([N:17]2[C:26]3[C:21](=[CH:22][C:23]([F:30])=[C:24](F)[C:25]=3[O:27][CH3:28])[C:20](=[O:31])[C:19]([C:32]([OH:34])=[O:33])=[CH:18]2)[CH2:16][CH2:15]1.[B](F)F.C(N(CC)CC)C>CS(C)=O.O>[ClH:4].[NH2:6][C@H:7]1[C@H:11]([O:12][CH3:13])[CH2:10][N:9]([C:24]2[C:25]([O:27][CH3:28])=[C:26]3[C:21]([C:20](=[O:31])[C:19]([C:32]([OH:34])=[O:33])=[CH:18][N:17]3[CH:14]3[CH2:16][CH2:15]3)=[CH:22][C:23]=2[F:30])[CH2:8]1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 139622Boron difluorideHCID 70194651-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acidHCID 10942334Sodium MethoxideHCID 67925434trans-3-Amino-4-methoxypyrrolidine dihydrochloride

생성물 1

HCID 679254237-(trans-3-Amino-4-methoxy-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

0.19 g (0.0036 mole) of sodium methoxide was added to a suspension of 0.34 g (0.0018 mole) of trans-3-amino-4-methoxypyrrolidine dihydrochloride (prepared as described in Preparation 18) in 1.5 ml of dimethyl sulfoxide, and the mixture was stirred at room temperature for 30 minutes. 0.31 g (0.0009 mole) of a chelate (IV) of 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid and boron difluoride (prepared as described in Preparation 7) were added to the resulting solution, followed by 0.27 g (0.0027 mole) of triethylamine. The mixture was then allowed to stand at room temperature overnight. At the end of this time, 50 ml of water were added to the mixture, and a chelate (V) separated out. This was collected by filtration to give yellow crystals. These were worked up in a similar manner to that described in Example 22, to give 0.22 g of 7-(trans-3-amino-4-methoxy-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-8-methoxy-1,4 -dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride as a fine yellow powder, melting at 192°-195° C.

후처리

  1. waitto stand at room temperature overnight
  2. customa chelate (V) separated out
  3. filtrationThis was collected by filtration
  4. customto give yellow crystals

출처 및 근거

ORD 기록
ord-eca6fc79925a4672b9db5fc69cf38e23
출처 데이터셋
uspto-grants-1991_03
특허 번호
US04997943

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