Dimethyl Sulfoxide → 3-Cyano-1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(4-hydroxypiperazin-1-yl)-4-oxoquinoline

HRID 1788982Notes

Reaction equation

Cl.Cl.[OH:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.CS(C)=O.C(N(CC)CC)C.[CH:21]1([N:24]2[C:33]3[C:28](=[CH:29][C:30]([F:36])=[C:31](F)[C:32]=3[F:34])[C:27](=[O:37])[C:26]([C:38]#[N:39])=[CH:25]2)[CH2:23][CH2:22]1>O>[C:38]([C:26]1[C:27](=[O:37])[C:28]2[C:33](=[C:32]([F:34])[C:31]([N:7]3[CH2:8][CH2:9][N:4]([OH:3])[CH2:5][CH2:6]3)=[C:30]([F:36])[CH:29]=2)[N:24]([CH:21]2[CH2:22][CH2:23]2)[CH:25]=1)#[N:39]

Participants

Conditions

Temperature: 100 °C

Procedure

1-Hydroxypiperazine dihydrochloride (2.45 g) (which is prepared in Preparation 1), dimethylsulfoxide (20 ml) and triethylamine (5.05 g) are added to 1-cyclopropyl-3-cyano-1,4-dihydro-4-oxo-6,7,8-trifluoroquinoline (2.64 g), which is prepared in Preparation 3, and the mixture is stirred with heating at 100° C. for 4 hours. After cooling to room temperature, water (300 ml) is added to the reaction mixture, and the resulting precipitate is filtered and washed with water to afford 3-cyano-1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(4-hydroxypiperazin-1-yl)-4-oxoquinoline (2.84 g) as pale yellow powder. The powder is recrystallized from dimethylsulfoxide to yield light brown needles, m.p. about 214° C. (decomposition).

Workup

customis prepared in Preparation 3
temperatureAfter cooling to room temperature
filtrationthe resulting precipitate is filtered
washwashed with water

Sources & evidence

ORD record: ord-f0baf9bc98584eac840fbefba23d905c
Source dataset: uspto-grants-1987_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04686221

Reaction notes

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