Triethylamine → HCID 59002950, compound

HRID 561103Notes

Reaction equation

[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[CH:16]1[CH2:18][CH2:17]1.[CH3:23][N:24]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)[CH2:25][CH2:26][NH:27][CH3:28].C(N(CC)CC)C>CS(C)=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:27]([CH3:28])[CH2:26][CH2:25][N:24]([CH3:23])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[CH:16]1[CH2:18][CH2:17]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid (400 mg, 1.44 mmol), N,N′-dimethyl-N-(2-pyridyl)-1,2-ethanediamine (355 mg, 2.15 mmol) and triethylamine (0.300 mL, 2.15 mmol) in anhydrous DMSO (6 mL) was stirred at 100° C. for 3 h. Triethylamine (0.300 mL, 2.15 mmol) was added and the mixture was stirred at 100° C. for 3 h. After cooling, the reaction mixture was poured into ice-water (50 mL). The resulting precipitate was collected by filtration, washed with water and dried to give 5-Amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[methyl[2-[methyl(2-pyridyl)amino]ethyl]amino]-4-oxoquinoline-3-carboxylic acid (480 mg, 73%) as a brown solid.

Workup

stirringthe mixture was stirred at 100° C. for 3 h
temperatureAfter cooling
filtrationThe resulting precipitate was collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-c0226aa61f904ec8afc753329e68e047
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063221B2

Reaction notes

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