N-Methylethylamine → HCID 86715593, compound

HRID 928739Notes

Reaction equation

HRID 928739 reaction equation
[N:1]1([C:6]2[CH:25]=[CH:24][C:9]([CH2:10][C:11]3[C:12](Cl)=[N:13][C:14]4[C:19]([C:20]=3[Cl:21])=[CH:18][C:17]([Br:22])=[CH:16][CH:15]=4)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[CH2:26]([NH:28][CH3:29])[CH3:27]>CN(C=O)C>[N:1]1([C:6]2[CH:25]=[CH:24][C:9]([CH2:10][C:11]3[C:12]([N:28]([CH2:26][CH3:27])[CH3:29])=[N:13][C:14]4[C:19]([C:20]=3[Cl:21])=[CH:18][C:17]([Br:22])=[CH:16][CH:15]=4)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 12219N-MethylethylamineHCID 867155943-(4-(1H-pyrazol-1-yl)benzyl)-6-bromo-2,4-dichloroquinoline2×

Product 1

HCID 86715593HCID 86715593, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(4-(1H-pyrazol-1-yl)benzyl)-6-bromo-2,4-dichloroquinoline (Intermediate 6: step c, 0.100 g, 0.231 mmol), N-ethylmethylamine (1.5 mL) and DMF (0.5 mL) were heated in a sealed tube at 80° C. for 8 hours, cooled to room temperature, evaporated in vacuo, diluted with acetonitrile and filtered. The filtrate was evaporated in vacuo and chromatographed (EtOAc/Heptane) to provide the title compound.

Workup

  1. temperaturecooled to room temperature
  2. customevaporated in vacuo
  3. additiondiluted with acetonitrile
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customchromatographed (EtOAc/Heptane)

Sources & evidence

ORD record
ord-aba86bbb0d9c4c939589fce77709ebf8
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

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