Hydrochloric Acid → 7-(1-Amino-6-azaspiro[2.5]oct-6-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, hydrochloride salt

HRID 1654515Notes

Reaction equation

HRID 1654515 reaction equation
C(OC([NH:8][CH:9]1[C:11]2([CH2:16][CH2:15][N:14]([C:17]3[N:26]=[C:25]4[C:20]([C:21](=[O:40])[C:22]([C:35]([O:37]CC)=[O:36])=[CH:23][N:24]4[C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=4[F:34])=[CH:19][C:18]=3[F:41])[CH2:13][CH2:12]2)[CH2:10]1)=O)(C)(C)C.[ClH:42]>C(OCC)(=O)C>[ClH:42].[NH2:8][CH:9]1[C:11]2([CH2:12][CH2:13][N:14]([C:17]3[N:26]=[C:25]4[C:20]([C:21](=[O:40])[C:22]([C:35]([OH:37])=[O:36])=[CH:23][N:24]4[C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=4[F:34])=[CH:19][C:18]=3[F:41])[CH2:15][CH2:16]2)[CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 152821727-(1-tert-Butoxycarbonylamino-6-azaspiro[2.5]oct-6-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carbOxylic acid, ethyl ester

Product 1

HCID 1317189627-(1-Amino-6-azaspiro[2.5]oct-6-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, hydrochloride saltYield 38%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the compound of step A (441 mg, 0.77 mmol) in ethyl acetate (9 ml) and 3N hydrogen chloride (9 ml) was heated to reflux overnight. solvents were removed in vacuo and the residue was recrystallized from methanolacetonitrile to give the title product as a yellow solid, mp 217° C. (decomap.), (133 mg, 0.29 mmol, 38% yield).

Workup

  1. temperatureto reflux overnight
  2. customsolvents were removed in vacuo
  3. customthe residue was recrystallized from methanolacetonitrile

Sources & evidence

ORD record
ord-7ac4bc56156e46499f4e2d2c29192668
Source dataset
uspto-grants-1995_04
Patent number
US05407943

Reaction notes

Loading…