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Chloropyrazine → HCID 54218343, compound

HRID 1858100
Notes
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Reaction equation

HRID 1858100 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].Cl[C:39]1[CH:44]=[N:43][CH:42]=[CH:41][N:40]=1>C(OCC)(=O)C.[Br-].[Zn+2].[Br-]>[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]([NH:27][C:39]3[CH:44]=[N:43][CH:42]=[CH:41][N:40]=3)[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

5

Reactant 2

HCID 73277ChloropyrazineHCID 54025520HCID 54025520, compound

Product 1

HCID 54218343HCID 54218343, compound

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To a suspension of 2-{2-[6-amino-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (prepared essentially as described in Example 1, 100 mg in 1 mL chloropyrazine) was added 500 mg zinc bromide and the mixture heated to 150° C. on an oil bath. After 3 hours, the mixture was cooled to room temperature, diluted with ethyl acetate and filtered through diatomaceous earth. The volatile organics were removed in vacuo and the residue dissolved in ethyl acetate, washed with water and the organic portion dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (ethyl acetate:hexane, 1:1) to give the title compound (12 mg).

Workup

  1. customprepared essentially
  2. temperaturethe mixture was cooled to room temperature
  3. filtrationfiltered through diatomaceous earth
  4. customThe volatile organics were removed in vacuo
  5. dissolutionthe residue dissolved in ethyl acetate
  6. washwashed with water
  7. dry with materialthe organic portion dried over sodium sulfate
  8. customPurification of the
  9. concentrationconcentrate by flash chromatography on silica gel (ethyl acetate:hexane, 1:1)

Sources & evidence

ORD record
ord-e55501bd3aa24cef9989e7c24aaa2c94
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