Hydrochloric Acid → 7-[3-[(2-Amino-1-oxopropyl)amino]-1-pyrrolidinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, monohydrochloride

HRID 232040Notes

Reaction equation

HRID 232040 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:33])=[C:11]([N:15]4[CH2:19][CH2:18][CH:17]([NH:20][C:21](=[O:32])[CH:22]([NH:24]C(OC(C)(C)C)=O)[CH3:23])[CH2:16]4)[C:12]=3[F:14])[C:7](=[O:34])[C:6]([C:35]([OH:37])=[O:36])=[CH:5]2)[CH2:3][CH2:2]1.[ClH:38]>C(O)C>[ClH:38].[NH2:24][CH:22]([CH3:23])[C:21]([NH:20][CH:17]1[CH2:18][CH2:19][N:15]([C:11]2[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:34])[C:6]([C:35]([OH:37])=[O:36])=[CH:5][N:4]3[CH:1]3[CH2:2][CH2:3]3)=[CH:9][C:10]=2[F:33])[CH2:16]1)=[O:32]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14555456HCID 14555456, compound

Product 1

HCID 678373217-[3-[(2-Amino-1-oxopropyl)amino]-1-pyrrolidinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, monohydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.3 g of (4.4 mmol) of 1-Cyclopropyl-7-[3-[[2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxopropyl]amino]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in a mixture of 25 ml of 1.0M hydrochloric acid and 25 ml of ethanol was heated at reflux for two hours. The mixture was evaporated to dryness in vacuo and the residue was triturated with ethanol/ether (100 ml/1:1). The solid was removed by filtration, washed with ethanol/ether, ether and dried in vacuo to give 1.6 g of the title compound, mp 238°-240°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for two hours
  3. customThe mixture was evaporated to dryness in vacuo
  4. customthe residue was triturated with ethanol/ether (100 ml/1:1)
  5. customThe solid was removed by filtration
  6. washwashed with ethanol/ether, ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-b70fc18bb6e749c497ecce5314bf686d
Source dataset
uspto-grants-1989_07
Patent number
US04851418

Reaction notes

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