Triethylamine → 1,4-Dihydro-7-(trans-3-methoxy-4-methylamino-1-pyrrolidinyl)-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid ethyl ester

HRID 398846노트

반응식

HRID 398846 반응식
C(N(CC)CC)C.[CH2:8]([O:10][C:11]([C:13]1[C:22](=[O:23])[C:21]2[C:16](=[N:17][C:18](Cl)=[CH:19][CH:20]=2)[N:15]([C:25]2[S:26][CH:27]=[CH:28][N:29]=2)[CH:14]=1)=[O:12])[CH3:9].Cl.Cl.[CH3:32][O:33][C@H:34]1[C@H:38]([NH:39][CH3:40])[CH2:37][NH:36][CH2:35]1>C(#N)C>[CH2:8]([O:10][C:11]([C:13]1[C:22](=[O:23])[C:21]2[C:16](=[N:17][C:18]([N:36]3[CH2:37][C@@H:38]([NH:39][CH3:40])[C@H:34]([O:33][CH3:32])[CH2:35]3)=[CH:19][CH:20]=2)[N:15]([C:25]2[S:26][CH:27]=[CH:28][N:29]=2)[CH:14]=1)=[O:12])[CH3:9]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 46928270Ethyl 7-chloro-4-oxo-1-(thiazol-2-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylateHCID 70201966trans-3-Methoxy-4-methylaminopyrrolidine dihydrochloride

생성물 1

HCID 702014441,4-Dihydro-7-(trans-3-methoxy-4-methylamino-1-pyrrolidinyl)-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid ethyl ester수율 67.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Triethylamine (18 ml) was added to a suspension composed of 7-chloro-1,4-dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid ethyl ester (7.1 g) obtained in Example A-1 (4), trans-3-methoxy-4-methylaminopyrrolidine dihydrochloride (6.0 g) and acetonitrile (150 ml). The resulting reaction mixture was stirred at room temperature for 5 hours, and was then concentrated under reduced pressure. Then, an aqueous solution of sodium hydrogencarbonate was added, and the resultant mixture was extracted with chloroform. After the obtained extract was dried over anhydrous sodium sulfate, solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel column chromatography (eluent chloroform:methanol=6:1), and thus, there was obtained 1,4-dihydro-7-(trans-3-methoxy-4-methylamino-1-pyrrolidinyl)-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid ethyl ester (6.1 g).

후처리

  1. customThe resulting reaction mixture
  2. concentrationwas then concentrated under reduced pressure
  3. additionThen, an aqueous solution of sodium hydrogencarbonate was added
  4. extractionthe resultant mixture was extracted with chloroform
  5. extractionAfter the obtained extract
  6. dry with materialwas dried over anhydrous sodium sulfate, solvent
  7. distillationwas distilled off under reduced pressure
  8. customthe resultant residue was purified by silica gel column chromatography (eluent chloroform:methanol=6:1)

출처 및 근거

ORD 기록
ord-03e7a00dcf16401187e0ada8395440e7
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05817669

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