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Pyridine → HCID 53873218, compound

HRID 1858074
Notes
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Reaction equation

HRID 1858074 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:28])=[C:24]([NH2:27])[CH:25]=2)[NH:20][C:19](=[O:29])[C:18]=1[C:30]1[CH:35]=[C:34]([CH3:36])[CH:33]=[C:32]([CH3:37])[CH:31]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:38](Cl)(Cl)=[O:39].N1C=CC=CC=1.Cl.C[O:50][C:51](=O)[CH2:52][NH:53][CH3:54]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:28])=[C:24]([N:27]3[C:51](=[O:50])[CH2:52][N:53]([CH3:54])[C:38]3=[O:39])[CH:25]=2)[NH:20][C:19](=[O:29])[C:18]=1[C:30]1[CH:31]=[C:32]([CH3:37])[CH:33]=[C:34]([CH3:36])[CH:35]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 54025520HCID 54025520, compound

Product 1

HCID 53873218HCID 53873218, compound

Reagents, catalysts & solvents 2

HCID 1140
Toluene
Solvent
HCID 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 tert-butyl ester (53 mg in 2 mL dry methylene chloride) at 0° C. was added phosgene (0.077 mL of a 1.93 M solution in toluene) followed by 0.016 mL of pyridine and the mixture stirred for 1 hour at 0° C. At this time, 70 mg of sarcosine methyl ester hydrochloride was added and the mixture allowed to warm to room temperature. After 20 hours, the mixture was diluted with ethyl acetate (15 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-ef41914e757044989d741adf70e3a890
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