Hydrochloric Acid → PD-117596 hydrochloride

HRID 978526Notes

Reaction equation

HRID 978526 reaction equation
C(OC([NH:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]([F:24])=[C:22]3[C:17]([C:18](=[O:31])[C:19]([C:28]([OH:30])=[O:29])=[CH:20][N:21]3[CH:25]3[CH2:27][CH2:26]3)=[CH:16][C:15]=2[F:32])[CH2:10]1)=O)(C)(C)C.[ClH:33]>C(O)(=O)C>[ClH:33].[NH2:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]([F:24])=[C:22]3[C:17]([C:18](=[O:31])[C:19]([C:28]([OH:30])=[O:29])=[CH:20][N:21]3[CH:25]3[CH2:26][CH2:27]3)=[CH:16][C:15]=2[F:32])[CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 137728007-[3-t-Butoxycarbonylamino-1-pyrrolidinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid

Product 1

HCID 13590048PD-117596 hydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 72.4 g (0.16 mole) of 7-[3-t-butoxycarbonylamino-1-pyrrolidinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 375 ml of 6 M hydrochloric acid, and 750 ml of glacial acetic acid was heated at 60° C. for four hours and the resulting solution was stirred at room temperature for 18 hours. The reaction was filtered through a fiber glass pad to clarify and the filtrate was evaporated in vacuo. The residue was triturated with 600 ml of ethanol:ether (1:1), the solid removed by filtration, washed with ethanol:ether (1:1), ether and dried in vacuo to give 63.8 g (98%) of the title compound, mp 313°-315° C.

Workup

  1. filtrationThe reaction was filtered through a fiber glass pad
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was triturated with 600 ml of ethanol:ether (1:1)
  4. customthe solid removed by filtration
  5. washwashed with ethanol:ether (1:1), ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-c3ca606e3c9b4bb6aa016c43636cbc2c
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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