Ethyl isocyanatoacetate → N-{[(2RS,6SR)-4-(1-Cyclopropyl-3-{[(2,4-dichlorobenzyl)amino]carbonyl}-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinolin-7-yl)-2,6-dimethylpiperazin-1-yl]carbonyl}glycine ethyl ester

HRID 2099322Notes

Reaction equation

HRID 2099322 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:24])=[C:11]([N:16]4[CH2:21][CH:20]([CH3:22])[NH:19][CH:18]([CH3:23])[CH2:17]4)[C:12]=3[O:14][CH3:15])[C:7](=[O:25])[C:6]([C:26]([NH:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=3[Cl:37])=[O:27])=[CH:5]2)[CH2:3][CH2:2]1.[N:38]([CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])=[C:39]=[O:40]>ClCCl>[CH2:45]([O:44][C:42](=[O:43])[CH2:41][NH:38][C:39]([N:19]1[CH:18]([CH3:23])[CH2:17][N:16]([C:11]2[C:12]([O:14][CH3:15])=[C:13]3[C:8]([C:7](=[O:25])[C:6]([C:26]([NH:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=4[Cl:37])=[O:27])=[CH:5][N:4]3[CH:1]3[CH2:3][CH2:2]3)=[CH:9][C:10]=2[F:24])[CH2:21][CH:20]1[CH3:22])=[O:40])[CH3:46]

Participants

4

Reactant 2

HCID 76283Ethyl isocyanatoacetateHCID 668599621-Cyclopropyl-N-(2,4-dichlorobenzyl)-7-[(3RS,5SR)-3,5-dimethylpiperazin-1-yl]-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxamide

Product 1

HCID 68976051N-{[(2RS,6SR)-4-(1-Cyclopropyl-3-{[(2,4-dichlorobenzyl)amino]carbonyl}-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinolin-7-yl)-2,6-dimethylpiperazin-1-yl]carbonyl}glycine ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 mg (0.18 mmol) of the compound from Example 39A are added to a solution of 25 mg (0.22 mmol) of ethyl isocyanatoacetate in 5 ml of dichloromethane. The reaction mixture is stirred at RT overnight. After the removal of the solvent on a rotary evaporator, the residue is purified by RP-HPLC (method 6). 73 mg (59% of theory) of the title compound are obtained.

Workup

  1. customAfter the removal of the solvent
  2. customon a rotary evaporator
  3. customthe residue is purified by RP-HPLC (method 6)

Sources & evidence

ORD record
ord-f74f1d042d284c309efeb6ae025bfe4e
Source dataset
uspto-grants-2009_08
Patent number
US07569563B2

Reaction notes

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