Sodium Hydroxide → HCID 44192503, compound

HRID 1855336Notes

Reaction equation

HRID 1855336 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[C:6]([F:9])[C:7]=1[F:8].[H-].[Na+].Cl[C:14]1[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]3)=[C:24]([O:34][CH3:35])[CH:23]=2)[N:15]=1.[OH-].[Na+]>CN1CCCC1=O>[CH3:35][O:34][C:24]1[CH:23]=[C:22]([NH:21][C:16]2[N:17]=[C:18]([CH3:20])[CH:19]=[C:14]([O:10][C:4]3[CH:3]=[C:2]([F:1])[C:7]([F:8])=[C:6]([F:9])[CH:5]=3)[N:15]=2)[CH:27]=[CH:26][C:25]=1[N:28]1[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 27779433,4,5-TrifluorophenolHCID 57829826HCID 57829826, compound

Product 1

HCID 44192503HCID 44192503, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

To a solution of 3,4,5-trifluorophenol (33 mg, 0.22 mmol) in 1-methyl-2-pyrrolidone (2 mL) was added at 20° C. under an atmosphere of nitrogen a 55% dispersion of sodium hydride in oil (10 mg, 0.22 mmol). The reaction was stirred for 30 min and then, (4-chloro-6-methyl-pyrimidin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine (66 mg, 0.2 mmol) was added. The mixture was heated in a microwave oven to 200° C. for 30 min and then poured onto 1 N aqueous sodium hydroxide solution. The mixture was stirred for 15 min, and the precipitate formed was filtered off, washed with water and dried to yield the title compound (72 mg, 8%) as a pale-brown solid.

Workup

  1. stirringThe mixture was stirred for 15 min
  2. customthe precipitate formed
  3. filtrationwas filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-8ad365f9f6234aeeba226b72a7c0fcf3
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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