7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid → 1-Cyclopropyl-6-fluoro-1,4-dihydro-7-(4-methylamino-1,3,3a,4,7,7a-hexahydro-isoindol-2-yl)-4-oxo-1,8-naphthyridine-3-carboxylic acid

HRID 128530Notes

Reaction equation

HRID 128530 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:19].[CH3:20][NH:21][CH:22]1[CH:30]=[CH:29][CH2:28][CH:27]2[CH:23]1[CH2:24][NH:25][CH2:26]2>C(#N)C>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:19])=[C:2]([N:25]4[CH2:24][CH:23]5[CH:27]([CH2:28][CH:29]=[CH:30][CH:22]5[NH:21][CH3:20])[CH2:26]4)[N:11]=3)[C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8]2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 110551427-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 15283247HCID 15283247, compound

Product 1

HCID 193743901-Cyclopropyl-6-fluoro-1,4-dihydro-7-(4-methylamino-1,3,3a,4,7,7a-hexahydro-isoindol-2-yl)-4-oxo-1,8-naphthyridine-3-carboxylic acidYield 100.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

282 mg (1 mmol) of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid are stirred in 3 ml of acetonitrile with 310 mg (2 mmol) of 4-methylamino-1,3,3a,4,7,7a-hexahydro-isoindole at room temperature for 1 hour. The undissolved solid is filtered off with suction, washed with water and acetonitrile and dried at 120° C. under a high vacuum. 0.4 g of 1-cyclopropyl-6-fluoro-1,4-dihydro-7-(4-methylamino-1,3,3a,4,7,7a-hexahydro-isoindol-2-yl)-4-oxo-1,8-naphthyridine-3-carboxylic acid is obtained as a crude product, which is dissolved in 5 ml of half-concentrated hydrochloric acid under the influence of heat. The hydrochloride is precipitated by addition of ethanol, filtered off with suction and dried at 120° C. under a high vacuum.

Workup

  1. filtrationThe undissolved solid is filtered off with suction
  2. washwashed with water and acetonitrile
  3. customdried at 120° C. under a high vacuum

Sources & evidence

ORD record
ord-ca3cb30b54a44f07a9063ab89c3a4c2b
Source dataset
uspto-grants-1995_11
Patent number
US05464796

Reaction notes

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