Phenyl chloroformate → 7-Chloro-4-oxo-3-(phenoxycarbonylamino-methyl)-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester

HRID 1887980Notes

Reaction equation

HRID 1887980 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1[N:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:8]2[C:13]([C:14](=[O:18])[C:15]=1[CH2:16][NH2:17])=[CH:12][CH:11]=[C:10]([Cl:19])[CH:9]=2)=[O:5].Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:28].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH3:2][O:3][C:4]([C:6]1[N:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:8]2[C:13]([C:14](=[O:18])[C:15]=1[CH2:16][NH:17][C:27]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:28])=[CH:12][CH:11]=[C:10]([Cl:19])[CH:9]=2)=[O:5]

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 81531DiisopropylethylamineHCID 712085323-Aminomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester hydrochloride2×

Product 1

HCID 718111377-Chloro-4-oxo-3-(phenoxycarbonylamino-methyl)-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-aminomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester hydrochloride (intermediate I) (0.050 g, 0.130 mmol), phenyl chloroformate (0.020 mL, 0.59 mmol) and N,N-diisopropylethylamine (0.10 mL, 0.574 mmol) in CH2Cl2 (10 mL) was stirred at room temperature, then concentrated to dryness. The crude product was purified using preparative reverse-phase HPLC to provide 7-chloro-4-oxo-3-(phenoxycarbonylamino-methyl)-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester. MS calcd. for C25H20ClN2O5 [(M+H)+] 463.1, obsd. 462.9.

Workup

  1. concentrationconcentrated to dryness
  2. customThe crude product was purified

Sources & evidence

ORD record
ord-6b821c3e53014b93871f911283a78010
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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