Hydrochloric Acid → HCID 461417, compound

HRID 1198580Notes

Reaction equation

HRID 1198580 reaction equation
C(OC([NH:8][CH:9]([CH:11]1[CH2:15][CH2:14][N:13]([C:16]2[N:25]=[C:24]3[C:19]([C:20](=[O:32])[C:21]([C:29]([OH:31])=[O:30])=[CH:22][N:23]3[CH:26]3[CH2:28][CH2:27]3)=[CH:18][C:17]=2[F:33])[CH2:12]1)[CH3:10])=O)(C)(C)C.Cl>C(O)C>[NH2:8][CH:9]([CH:11]1[CH2:15][CH2:14][N:13]([C:16]2[N:25]=[C:24]3[C:19]([C:20](=[O:32])[C:21]([C:29]([OH:31])=[O:30])=[CH:22][N:23]3[CH:26]3[CH2:27][CH2:28]3)=[CH:18][C:17]=2[F:33])[CH2:12]1)[CH3:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19419131HCID 19419131, compound

Product 1

HCID 461417HCID 461417, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-[3-(1-[N-tert-butoxycarbonylamino]ethyl)-1-pyrrolidinyl]-1-cyclopropyl-6-fluoro-1,4 -dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid isomer B (0.74 g, 0.0016 mole) in ethanol (35 mL)/1N HCl (14 mL) was heated at 90° for two hours. The reaction was cooled to room temperature and the solvent was removed under reduced pressure. The residue was treated with isopropyl alcohol twice and the solvent was removed under reduced pressure. The solid was dried in an oven under vacuum at 70° for 60 hours. The solid was then stirred up in water, filtered, and the filtrate was placed on a freeze drying apparatus for 16 hours. 7-[3-(1-aminoethyl)-1-pyrrolidinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8 -naphthyridine-3-carboxylic acid isomer B was obtained (0.63 g, 80%) as a pale yellow solid, mp 281°-284° (dec).

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionThe residue was treated with isopropyl alcohol twice
  3. customthe solvent was removed under reduced pressure
  4. customThe solid was dried in an oven under vacuum at 70° for 60 hours
  5. filtrationfiltered
  6. customdrying apparatus for 16 hours

Sources & evidence

ORD record
ord-63db86bdeb4e48cf8566676bb0a9b924
Source dataset
uspto-grants-1994_01
Patent number
US05281612

Reaction notes

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