Sodium Cyanide → Ethyl 3-[(5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinolin-7-yl)amino]propionate

HRID 561105Notes

Reaction equation

HRID 561105 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:9]([O:21][CH3:22])=[C:8]2[C:3]=1[C:4](=[O:29])[C:5](C(O)=O)=[CH:6][N:7]2[CH:23]1[CH2:25][CH2:24]1.[C-]#N.[Na+]>>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:9]([O:21][CH3:22])=[C:8]2[C:3]=1[C:4](=[O:29])[CH:5]=[CH:6][N:7]2[CH:23]1[CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 8929Sodium CyanideHCID 24754257HCID 24754257, compound

Product 1

HCID 24754259Ethyl 3-[(5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinolin-7-yl)amino]propionateYield 63%

Conditions

Temperature
120 °C

Procedure

A mixture of 5-amino-1-cyclopropyl-7-[2-(ethoxycarbonyl)ethyl amino]-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid (1.30 g, 3.19 mmol) and NaCN (1.57 g, 32.0 mmol) in DSMO (25 mL) was stirred at 120° C. for 2 h. After cooling, the reaction mixture was poured in to ice-water (300 mL) and extracted with EtOAc (3×100 mL). The organic layers were combined, washed with water (3×100 mL) and brine (100 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (Chromatorex NH-DM2035 (Fuji Sylysia Chemical Co., Ltd.), hexane:EtOAc 1:1) to give ethyl 3-[(5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinolin-7-yl)amino]propionate (723 mg, 63%) as a pale yellow solid.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc (3×100 mL)
  3. washwashed with water (3×100 mL) and brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (Chromatorex NH-DM2035 (Fuji Sylysia Chemical Co., Ltd.), hexane:EtOAc 1:1)

Sources & evidence

ORD record
ord-6d989ae8cdf64af5a45caabc93780525
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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