1,8-Diazabicyclo[5.4.0]undec-2-ene → HCID 22121171, compound

HRID 1274746Notes

Reaction equation

HRID 1274746 reaction equation
Cl.Cl.[NH2:3][CH:4]1[CH2:7][NH:6][CH2:5]1.N12CCCNC1CCCC=C2.[NH2:19][C:20]1[N:25]=[C:24]([N:26]2[C:35]3[C:30](=[CH:31][C:32]([F:38])=[C:33](F)[C:34]=3[CH3:36])[C:29](=[O:39])[C:28]([C:40]([OH:42])=[O:41])=[CH:27]2)[C:23]([F:43])=[CH:22][C:21]=1[F:44]>N1C=CC=CC=1>[NH2:3][CH:4]1[CH2:7][N:6]([C:33]2[C:34]([CH3:36])=[C:35]3[C:30]([C:29](=[O:39])[C:28]([C:40]([OH:42])=[O:41])=[CH:27][N:26]3[C:24]3[C:23]([F:43])=[CH:22][C:21]([F:44])=[C:20]([NH2:19])[N:25]=3)=[CH:31][C:32]=2[F:38])[CH2:5]1

Participants

5

Reactant 3

HCID 98128211,8-Diazabicyclo[5.4.0]undec-2-eneHCID 12042412HCID 12042412, compoundHCID 13491919Azetidin-3-amine--hydrogen chloride (1/2)

Product 1

HCID 22121171HCID 22121171, compoundYield 10.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 70 mg of 3-aminoazetidine dihydro-chloride, 200 mg of 1,8-diazabicyclo[5,4,0]undecene, and 300 mg of pyridine was stirred at 100° C., and 110 mg of 1-(6-amino-3,5-difluoropyridine-2-yl)-6,7-difluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid was added to the solution and the solution was stirred at 100° C. for 6 minutes. The solvent was distilled off the reaction solution, and to the residue was added one drop of acetic acid and 3 ml of ethanol with heating, and the solution was allowed to stand. The solid precipitate was collected and dried to obtain 13 mg of the title compound as a pale yellow powder.

Workup

  1. distillationThe solvent was distilled off the reaction solution
  2. additionto the residue was added one drop of acetic acid and 3 ml of ethanol
  3. temperaturewith heating
  4. customThe solid precipitate was collected
  5. customdried

Sources & evidence

ORD record
ord-e6ba789c594a41679fad3093fc7e8762
Source dataset
uspto-grants-2000_12
Patent number
US06156903

Reaction notes

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