1-pyrimidin-2-yl-1,4-diazepane → HCID 15887898, compound

HRID 1636280Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:13]([F:16])([F:15])[F:14])[C:11]=1F)[N:8]([CH3:17])[CH:7]=[C:6]([C:18]([OH:20])=[O:19])[C:5]2=[O:21].[N:22]1[CH:27]=[CH:26][CH:25]=[N:24][C:23]=1[N:28]1[CH2:34][CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:13]([F:15])([F:16])[F:14])[C:11]=1[N:31]1[CH2:32][CH2:33][CH2:34][N:28]([C:23]3[N:22]=[CH:27][CH:26]=[CH:25][N:24]=3)[CH2:29][CH2:30]1)[N:8]([CH3:17])[CH:7]=[C:6]([C:18]([OH:20])=[O:19])[C:5]2=[O:21]

Participants

Conditions

Temperature: 105 °C

Procedure

In 12 ml of pyridine were dissolved 0.8 g (0.0026 mole) of 6,7-difluoro-8-trifluoromethyl-1,4-dihydro-1-methyl-4-oxoquinoline-3-carboxylic acid and 2.1 g (0.0118 mole) of 1-(2-pyrimidinyl)homopiperazine, the mixture was stirred at 105° C. for 3 hours, and then the solvent was removed by evaporation under reduced pressure. The residue was applied to silica gel column chromatography (eluent; a chloroform:methanol=9.5:0.5 mixed solution) to obtain 0.45 g of 6-fluoro-8-trifluoromethyl-1,4-dihydro-4-oxo-1-methyl-7-[4-(2-pyrimidinyl)homopiperazin-1-yl)quinoline-3-carboxylic acid as yellow powder.

Workup

customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record: ord-c245ba3eeb2e4f4d890baef852b73db7
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06034086

Reaction notes

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