Diisopropylethylamine → HCID 90410235, compound

HRID 1527762Notes

Reaction equation

HRID 1527762 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:10]([O-:12])=[O:11])=[C:7]([CH:9]=1)[NH2:8].[Br:13][C:14]1[CH:21]=[C:20]([F:22])[C:17]([CH2:18]N)=[C:16]([F:23])[CH:15]=1.CCN(C(C)C)C(C)C>C(#N)C>[Br:13][C:14]1[CH:21]=[C:20]([F:22])[C:17]([CH2:18][NH:8][C:7]2[CH:9]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[N+:10]([O-:12])=[O:11])=[C:16]([F:23])[CH:15]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 853005-Methoxy-2-nitroanilineHCID 40427035HCID 40427035, compound

Product 1

HCID 90410235HCID 90410235, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-methoxy-2-nitroaniline (513 mg, 3 mmol), 4-bromo-2,6-difluorobenzyl amine (616 g, 3 mmol), DIPEA (1.55 mL, 9 mmol) and acetonitrile (10 mL) was heated to 130-150° Celsius for 16 h. The mixture was then cooled to RT and concentrated to dryness. To the residue was added H2O (100 mL) and the resulting solid was collected by filtration and dried to afford the title compound (900 mg, 80.1%).

Workup

  1. temperatureThe mixture was then cooled to RT
  2. concentrationconcentrated to dryness
  3. additionTo the residue was added H2O (100 mL)
  4. filtrationthe resulting solid was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-16a553ac985c46d1902dece2afea2bd9
Source dataset
uspto-grants-2015_07
Patent number
US09089569B2

Reaction notes

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