Hydrochloric Acid → HCID 24754257, compound

HRID 561104Notes

Reaction equation

HRID 561104 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.Cl.[CH2:24]([O:26][C:27](=[O:31])[CH2:28][CH2:29][NH2:30])[CH3:25].C(N(CC)CC)C.Cl>CS(C)=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:30][CH2:29][CH2:28][C:27]([O:26][CH2:24][CH3:25])=[O:31])[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 105668945-Amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 24754257HCID 24754257, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

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 (1.50 g, 5.39 mmol), β-alanine ethyl ester hydrochloride (2.48 g, 16.1 mmol) and triethylamine (4.50 mL, 32.3 mmol) in anhydrous DMSO (30 mL) was stirred at 100° C. for 10 h. After cooling, the reaction mixture was poured into ice-water (50 mL) and acidified with 1M HCl. The product was extracted with EtOAc, washed with water and brine, dried over Na2SO4 and concentrated in vacuo. Trituration of the residue with MeOH (30 mL) gave 5-amino-1-cyclopropyl-7-[2-(ethoxycarbonyl)ethylamino]-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid (1.54 g, 70%) as a yellow solid.

Workup

  1. temperatureAfter cooling
  2. extractionThe product was extracted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-19cf643a6a054ebba14801df38e9c768
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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