Water → HCID 59002954, compound

HRID 561107Notes

Reaction equation

HRID 561107 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:13][CH2:14][CH2:15][NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][N:18]=2)[C:9]([O:28][CH3:29])=[C:8]2[C:3]=1[C:4](=[O:36])[C:5](C(O)=O)=[CH:6][N:7]2[CH:30]1[CH2:32][CH2:31]1.[C-]#N.[Na+].O>CS(C)=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:13][CH2:14][CH2:15][NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][N:18]=2)[C:9]([O:28][CH3:29])=[C:8]2[C:3]=1[C:4](=[O:36])[CH:5]=[CH:6][N:7]2[CH:30]1[CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 59003047HCID 59003047, compound

Product 1

HCID 59002954HCID 59002954, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-amino-1-cyclopropyl-7-[2-[(5-ethoxycarbonyl-2-pyridyl)amino]ethylamino]-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid (540 mg, 1.08 mmol) and NaCN (540 mg, 11.0 mmol) in DMSO (10 mL) was stirred at 120° C. for 2 h. After cooling, the reaction mixture was poured into water (100 mL) and extracted with EtOAc (2×50 mL). The organic layer washed with water (2×50 mL) and brine (50 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography (hexane: EtOAc 1:3) of the residue gave crude product as a brown oil (600 mg). The obtained oil was further purified by column chromatography (Chromatorex NH-DM2035 (Fuji Sylysia Chemical Co., Ltd.), hexane: EtOAc 1:3) to give ethyl 2-[2-[(5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinolin-7-yl)amino]ethylamino]pyridine-5-carboxylate (397 mg, 81%) as a yellow amorphous solid.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe organic layer washed with water (2×50 mL) and brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (hexane: EtOAc 1:3) of the residue
  7. customgave crude product as a brown oil (600 mg)
  8. customThe obtained oil was further purified by column chromatography (Chromatorex NH-DM2035 (Fuji Sylysia Chemical Co., Ltd.), hexane: EtOAc 1:3)

Sources & evidence

ORD record
ord-14246608e8e74057be432ba500e302be
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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