Hydrochloric Acid → 7-(5-Aminomethyl-2-isoindolinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride salt

HRID 1494822Notes

Reaction equation

HRID 1494822 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][C:11]([N:18]3[CH2:26][C:25]4[C:20](=[CH:21][CH:22]=[C:23]([CH2:27][NH:28]C(=O)C)[CH:24]=4)[CH2:19]3)=[C:12]([F:17])[CH:13]=2)[N:8]([CH:32]2[CH2:34][CH2:33]2)[CH:7]=1)=[O:5])C.[ClH:35]>C(O)C>[ClH:35].[NH2:28][CH2:27][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[CH2:19][N:18]([C:11]1[N:10]=[C:9]3[C:14]([C:15](=[O:16])[C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]3[CH:32]3[CH2:34][CH2:33]3)=[CH:13][C:12]=1[F:17])[CH2:26]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 572711897-(5-Acetamidomethyl-2-isoindolinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester

Product 1

HCID 679223597-(5-Aminomethyl-2-isoindolinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride salt

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

80 mg of 7-(5-acetamidomethyl-2-isoindolinyl)-1- cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester was dissolved in a mixture of 10 ml of 10% hydrochloric acid and 10 ml of ethanol. The mixture was heated under reflux for 24 hours. The precipitates deposited were collected by filtration and washed with water and ethanol in this order to obtain 68 mg of 7-(5-aminomethyl-2-isoindolinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride salt.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. filtrationThe precipitates deposited were collected by filtration
  4. washwashed with water and ethanol in this order

Sources & evidence

ORD record
ord-2ec7002a7a8d43619d56c391fd13a0db
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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