Pyridine → 7-fluoro-1-methyl-8-[[3-cyclopropylamino)methyl-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo-[3,2-a]quinoline-4-carboxylic acid

HRID 465008Notes

Reaction equation

HRID 465008 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:19])[C:7]([C:16]([OH:18])=[O:17])=[C:8]3[S:14][CH2:13][CH:12]([CH3:15])[N:9]32)=[CH:4][C:3]=1[F:20].[CH:21]1([NH:24][CH2:25][CH:26]2[CH2:30][CH2:29]NC2)[CH2:23][CH2:22]1.[N:31]1C=CC=C[CH:32]=1>>[F:20][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:31]1[CH2:32][CH2:29][CH2:30][CH:26]1[CH2:25][NH:24][CH:21]1[CH2:22][CH2:23]1)[N:9]1[CH:12]([CH3:15])[CH2:13][S:14][C:8]1=[C:7]([C:16]([OH:18])=[O:17])[C:6]2=[O:19]

Participants

4

Reactant 3

HCID 1049PyridineHCID 13491801N-(Pyrrolidin-3-ylmethyl)cyclopropanamineHCID 202614398-chloro-7-fluoro-1-methyl-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid

Product 1

HCID 704857577-fluoro-1-methyl-8-[[3-cyclopropylamino)methyl-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo-[3,2-a]quinoline-4-carboxylic acid

Procedure

A mixture of 3.14 g (10 mmol) of 8-chloro-7-fluoro-1-methyl-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid, 2.1 g (15 mmol) of N-cyclopropyl-3-pyrrolidinemethanamine and 50 ml of pyridine is heated at reflux for 24 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-1-methyl-8-[[3-cyclopropylamino)methyl-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo-[3,2-a]quinoline-4-carboxylic acid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 24 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-dbbab3cf8aae45698f01520c4bdea9f2
Source dataset
uspto-grants-1985_10
Patent number
US04550104

Reaction notes

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