Triethylamine → 9-Cyclopropyl-6,8-difluoro-7-(3-amino-3-methyl-1-azetidinyl)-2,3,4,9-tetrahydroisothiazolo[5,4-b]quinoline-3,4-dione

HRID 1534089Notes

Reaction equation

HRID 1534089 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]3[C:18](=[O:21])[NH:19][S:20][C:5]2=3)[CH2:3][CH2:2]1.Cl.Cl.[CH3:24][C:25]1([NH2:29])[CH2:28][NH:27][CH2:26]1.C(N(CC)CC)C>N1C=CC=CC=1>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:27]4[CH2:28][C:25]([NH2:29])([CH3:24])[CH2:26]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]3[C:18](=[O:21])[NH:19][S:20][C:5]2=3)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 146727459-Cyclopropyl-6,7,8-trifluoro-2,3,4,9-tetrahydroisothiazolo[5,4-b]quinoline-3,4-dioneHCID 148524533-Methylazetidin-3-amine dihydrochloride

Product 1

HCID 100225309-Cyclopropyl-6,8-difluoro-7-(3-amino-3-methyl-1-azetidinyl)-2,3,4,9-tetrahydroisothiazolo[5,4-b]quinoline-3,4-dioneYield 74.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 250 mg (0.8 mmol) of 9-cyclopropyl-6,7,8-trifluoro-2,3,4,9-tetrahydroisothiazolo[5,4-b]quinoline-3,4-dione, 255 mg (1.6 mmol) of 3-methyl-3-aminoazetidine dihydrochloride and 0.6 ml of triethylamine in 10 ml of pyridine is kept refluxing for 2 hours, the mixture is evaporated under vacuum, a mixture of ethanol with water is added, the resulting mixture is filtered and the product is washed. 0.225 g of 9-cyclopropyl-6,8-difluoro-7-(3-amino-3-methyl-1-azetidinyl)-2,3,4,9-tetrahydroisothiazolo[5,4-b]quinoline-3,4-dione, melting point 294°-300° C., is thereby obtained.

Workup

  1. temperatureis kept refluxing for 2 hours
  2. customthe mixture is evaporated under vacuum
  3. additiona mixture of ethanol with water
  4. additionis added
  5. filtrationthe resulting mixture is filtered
  6. washthe product is washed

Sources & evidence

ORD record
ord-b7f2a5ca1d8842acbe46d09ae28b1699
Source dataset
uspto-grants-1992_02
Patent number
US05087621

Reaction notes

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