Triethylamine → HCID 54189520, compound

HRID 398849Notes

Reaction equation

HRID 398849 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][C:11](Cl)=[CH:12][CH:13]=2)[N:8]([C:18]2[S:19][CH:20]=[C:21]([F:23])[N:22]=2)[CH:7]=1)=[O:5])[CH3:2].[C:24]([O:28][C:29]([NH:31][CH:32]1[CH2:36][CH2:35][NH:34][CH2:33]1)=[O:30])([CH3:27])([CH3:26])[CH3:25].C(N(CC)CC)C>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][C:11]([N:34]3[CH2:35][CH2:36][CH:32]([NH:31][C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:30])[CH2:33]3)=[CH:12][CH:13]=2)[N:8]([C:18]2[S:19][CH:20]=[C:21]([F:23])[N:22]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 54299941HCID 54299941, compound

Product 1

HCID 54189520HCID 54189520, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture composed of 7-chloro-1-(4-fluoro-2-thiazoly)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester (30 mg) obtained in Example A-2, 3-(t-butoxycarbonylamino)pyrrolidine (19 mg), triethylamine (26 mg) and acetonitrile (10 ml) was stirred at room temperature for 30 minutes. Solvent was distilled off under reduced pressure, and water was added, and then, the resulting mixture was extracted with chloroform. The obtained extract was dried over anhydrous sodium sulfate, and solvent was distilled off under reduced pressure. The resulting residue was subjected to recrystallization with use of ethyl acetate, and thus, there was obtained 7-(3-t-butoxycarbonylamino-1-pyrrolidinyl)-1-(4-fluoro-2-thiazolyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester (40 mg).

Workup

  1. distillationSolvent was distilled off under reduced pressure, and water
  2. additionwas added
  3. extractionthe resulting mixture was extracted with chloroform
  4. extractionThe obtained extract
  5. dry with materialwas dried over anhydrous sodium sulfate, and solvent
  6. distillationwas distilled off under reduced pressure
  7. customThe resulting residue was subjected to recrystallization with use of ethyl acetate

Sources & evidence

ORD record
ord-97c4dea930e944fe8d4b276b50f97fca
Source dataset
uspto-grants-1998_10
Patent number
US05817669

Reaction notes

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