Hydrochloric Acid → 1-Cyclopropyl-7-[5-(2,4-diamino-pyrimidin-5ylmethyl)-2,3-dimethoxy-phenylethynyl]-6,8-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid hydrochloride

HRID 963437Notes

Reaction equation

HRID 963437 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:36])=[C:11]([C:15]#[C:16][C:17]4[CH:22]=[C:21]([CH2:23][C:24]5[C:25]([NH2:31])=[N:26][C:27]([NH2:30])=[N:28][CH:29]=5)[CH:20]=[C:19]([O:32][CH3:33])[C:18]=4[O:34][CH3:35])[C:12]=3[F:14])[C:7](=[O:37])[C:6]([C:38]([O:40]CC)=[O:39])=[CH:5]2)[CH2:3][CH2:2]1.[OH-].[Na+].[ClH:45]>C(O)C>[ClH:45].[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:36])=[C:11]([C:15]#[C:16][C:17]4[CH:22]=[C:21]([CH2:23][C:24]5[C:25]([NH2:31])=[N:26][C:27]([NH2:30])=[N:28][CH:29]=5)[CH:20]=[C:19]([O:32][CH3:33])[C:18]=4[O:34][CH3:35])[C:12]=3[F:14])[C:7](=[O:37])[C:6]([C:38]([OH:40])=[O:39])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19081771Ethyl 1-cyclopropyl-7-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenylethynyl]-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylate

Product 1

HCID 699981461-Cyclopropyl-7-[5-(2,4-diamino-pyrimidin-5ylmethyl)-2,3-dimethoxy-phenylethynyl]-6,8-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid hydrochlorideYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.51 g of ethyl 1-cyclopropyl-7-[5-(2,4-diamino-pyrimidin-5ylmethyl)-2,3-dimethoxy-phenylethynyl]-6,8-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylate (Example 12a)) is held at reflux in 7 ml of ethanol and 7 ml of a 2N aqueous sodium hydroxide solution for one hour. The reaction mixture is cooled to room temperature and acidified with 25% aqueous hydrochloric acid. The precipitated substance is filtered off under suction, washed with 20 ml of water, 20 ml of ethanol and 20 ml of ether and dried. 444 mg (86%) of 1-cyclopropyl-7-[5-(2,4-diamino-pyrimidin-5ylmethyl)-2,3-dimethoxy-phenylethynyl]-6,8-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid hydrochloride are obtained as a colourless solid. M.p.>230°. Mass spectrum (ISP): peaks: inter alia at 548.5 (M++H, 100%).

Workup

  1. filtrationThe precipitated substance is filtered off under suction
  2. washwashed with 20 ml of water, 20 ml of ethanol and 20 ml of ether
  3. customdried

Sources & evidence

ORD record
ord-033c9ba673f64ee5809c6a8b3471ee75
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

Loading…