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 398846Notes

Reaction equation

HRID 398846 reaction equation
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]

Participants

5

Reactant 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

Product 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 esterYield 67.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-03e7a00dcf16401187e0ada8395440e7
Source dataset
uspto-grants-1998_10
Patent number
US05817669

Reaction notes

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