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4-Aminopyridine → 2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(3-pyridin-4-yl-ureido)-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester

HRID 1858066
Notes
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Reaction equation

HRID 1858066 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[CH2:17][CH2:18][O:19][C:20]1[C:29]2[C:24](=[CH:25][C:26]([Cl:31])=[C:27]([NH2:30])[CH:28]=2)[NH:23][C:22](=[O:32])[C:21]=1[C:33]1[CH:38]=[C:37]([CH3:39])[CH:36]=[C:35]([CH3:40])[CH:34]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:41](Cl)(Cl)=[O:42].C(N(CC)CC)C.[NH2:52][C:53]1[CH:58]=[CH:57][N:56]=[CH:55][CH:54]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[CH2:17][CH2:18][O:19][C:20]1[C:29]2[C:24](=[CH:25][C:26]([Cl:31])=[C:27]([NH:30][C:41]([NH:52][C:53]3[CH:58]=[CH:57][N:56]=[CH:55][CH:54]=3)=[O:42])[CH:28]=2)[NH:23][C:22](=[O:32])[C:21]=1[C:33]1[CH:38]=[C:37]([CH3:39])[CH:36]=[C:35]([CH3:40])[CH:34]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 17274-AminopyridineHCID 6371PhosgeneHCID 8471TriethylamineHCID 539323332-{2-[6-Amino-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 543905802-{2-[7-Chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(3-pyridin-4-yl-ureido)-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-{2-[6-amino-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester (200 mg in 5 mL dry methylene chloride) at 0° C. was added phosgene (0.3 mL of a 1.93 M solution in toluene) followed by 0.111 mL of triethylamine and the mixture stirred for 1 hour at 0° C. At this time, 188 mg of 4-aminopyridine was added and the mixture allowed to warm to room temperature. After 20 hours, the mixture was diluted with ethyl acetate (200 mL) and the reaction quenched by the addition of 10% citric acid. The organic portion was concentrated in vacuo to provide the crude title compound.

Workup

  1. temperatureto warm to room temperature
  2. waitAfter 20 hours
  3. customthe reaction quenched by the addition of 10% citric acid
  4. concentrationThe organic portion was concentrated in vacuo

Sources & evidence

ORD record
ord-a7092cb4323d443a9694f295e19df371
Source dataset
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06150352

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes