Water → HCID 59002902, compound

HRID 561143Notes

Reaction equation

HRID 561143 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9](F)[C:10]([F:25])=[C:11]([NH:15][CH2:16][CH2:17][NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[C:12]=3[F:14])[C:7](=[O:27])[CH:6]=[C:5]2[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:40][O:41][C:42]1[CH:49]=[CH:48][C:45]([CH2:46][NH2:47])=[CH:44][CH:43]=1.O>CS(C)=O>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([NH:47][CH2:46][C:45]4[CH:48]=[CH:49][C:42]([O:41][CH3:40])=[CH:43][CH:44]=4)[C:10]([F:25])=[C:11]([NH:15][CH2:16][CH2:17][NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[C:12]=3[F:14])[C:7](=[O:27])[CH:6]=[C:5]2[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 754524-MethoxybenzylamineHCID 59002828HCID 59002828, compound

Product 1

HCID 59002902HCID 59002902, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of ethyl 1-cyclopropyl-5,6,8-trifluoro-1,4-dihydro-4-oxo-7-[(2-pyridylamino)ethylamino]quinoline-2-carboxylate (705 mg, 1.58 mmol) and triethylamine (0.66 mL, 4.74 mmol) and 4-methoxybenzylamine (0.600 mL, 4.62 mmol) in DMSO (15 mL) was stirred at 100° C. for 18 h. The reaction mixture was poured into water, and then extracted with EtOAc. The organic layer washed with water and brine, and dried over anhyd. Na2SO4 followed by the removal of EtOAc. The crude product was purified by column chromatography (Hexane:EtOAc 1:1) to yield ethyl 1-cyclopropyl-6,8-difluoro-1,4-dihydro-5-(4-methoxybenzylamino)-4-oxo-7-[2-(2-pyridylamino)ethylamino]quinoline-2-carboxylate (597 mg, 67%) as a orange amorphous solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer washed with water and brine
  3. customdried over anhyd
  4. customNa2SO4 followed by the removal of EtOAc
  5. customThe crude product was purified by column chromatography (Hexane:EtOAc 1:1)

Sources & evidence

ORD record
ord-f9acca289ed0499e9fadeb4dfd0c8015
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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