tert-butyl N-(pyrrolidin-3-yl)carbamate → 7-fluoro-8-[3(-t-butoxycarbonylamino)-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid

HRID 465006Notes

Reaction equation

HRID 465006 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[C:8]3[S:14][CH2:13][CH2:12][N:9]32)=[CH:4][C:3]=1[F:19].[C:20]([O:24][C:25]([NH:27][CH:28]1[CH2:32][CH2:31][NH:30][CH2:29]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>N1C=CC=CC=1>[F:19][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:30]1[CH2:31][CH2:32][CH:28]([NH:27][C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])[CH2:29]1)[N:9]1[CH2:12][CH2:13][S:14][C:8]1=[C:7]([C:15]([OH:17])=[O:16])[C:6]2=[O:18]

Participants

4

Reactant 2

HCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 104700458-chloro-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)quinoline-4-carboxylic acid

Product 1

HCID 137262077-fluoro-8-[3(-t-butoxycarbonylamino)-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 9.0 g (30 mmol) of 8-chloro-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid, 8.37 g (45 mmol) of 3-(t-butoxycarbonylamino)pyrrolidine and 100 ml of pyridine is heated at reflux for 18 hours. The solvent is removed in vacuo and the residue triturated with water. The solid which forms is removed by filtration, washed with water and dried in vacuo to give 7-fluoro-8-[3(-t-butoxycarbonylamino)-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 18 hours
  3. customThe solvent is removed in vacuo
  4. customthe residue triturated with water
  5. customThe solid which forms is removed by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-94ddbb1d7654416caeab869901c8a0c5
Source dataset
uspto-grants-1985_10
Patent number
US04550104

Reaction notes

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