Water → HCID 59003047, compound

HRID 561106Notes

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.[NH2:23][CH2:24][CH2:25][NH:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:29][N:28]=1.C(N(CC)CC)C.O>CS(C)=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:23][CH2:24][CH2:25][NH:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:29][N:28]=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 (740 mg, 2.39 mmol), ethyl 2-(2-aminoethylamino)pyridine-5-carboxylate (1.00 g, 4.78 mmol) and triethylamine (0.670 mL, 4.81 mmol) in anhydrous DMSO (7 mL) was stirred at 100° C. for 8 h. After cooling, the reaction mixture was poured into water (300 mL) and extracted with CH2Cl2 (2×100 mL). The organic layers were combined, washed with water, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography (EtOAc) to give 5-amino-1-cyclopropyl-7-[2-[(5-ethoxycarbonyl-2-pyridyl)amino]ethylamino]-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid (600 mg, 50%) as a yellow solid.

Workup

temperatureAfter cooling
extractionextracted with CH2Cl2 (2×100 mL)
washwashed with water
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (EtOAc)

Sources & evidence

ORD record: ord-7fa7811af5454963880a74d5a3ea1dc7
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063221B2

Reaction notes

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