Diethyl Ether → HCID 53793803, compound

HRID 1415961Notes

Reaction equation

HRID 1415961 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17](Cl)[N:18]=3)[C:13](=[O:21])[C:12]([C:22]([OH:24])=[O:23])=[CH:11]2)[C:5]([F:9])=[CH:6][C:7]=1[F:8].Cl.Cl.[NH2:27][CH:28]1[CH2:31][NH:30][CH2:29]1.CN1CCCC1.C(OCC)C>C(#N)C.C(O)C>[NH2:27][CH:28]1[CH2:31][N:30]([C:17]2[N:18]=[C:19]3[C:14]([C:13](=[O:21])[C:12]([C:22]([OH:24])=[O:23])=[CH:11][N:10]3[C:4]3[C:5]([F:9])=[CH:6][C:7]([F:8])=[C:2]([NH2:1])[CH:3]=3)=[CH:15][CH:16]=2)[CH2:29]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 84541-MethylpyrrolidineHCID 13491919Azetidin-3-amine--hydrogen chloride (1/2)HCID 54017249HCID 54017249, compound

Product 1

HCID 53793803HCID 53793803, compoundYield 57.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

With stirring at 80° C., 100 mg of 1-(3-amino-4,6-difluorophenyl)-7-chloro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid was added to a solution of 61 mg of 3-aminoazetidine dihydrochloride and 119 mg of N-methylpyrrolidine in 3 ml of acetonitrile. The solution was stirred at 80° C. for 2 hours and 50 minutes. After the reaction solution was allowed to cool down, decantation with diethyl ether was carried out. The solid was dispersed by adding a small amount of ethanol and collected by filtration. The solid was washed with ethanol and then diethyl ether to give 63 mg of the title compound.

Workup

  1. stirringThe solution was stirred at 80° C. for 2 hours and 50 minutes
  2. temperatureto cool down
  3. additionThe solid was dispersed
  4. filtrationcollected by filtration
  5. washThe solid was washed with ethanol

Sources & evidence

ORD record
ord-8606939ef108499490b289669f10d16b
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

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