Methanol → HCID 59636156, compound

HRID 80185Notes

Reaction equation

HRID 80185 reaction equation
[CH3:1][NH:2][NH2:3].F[C:5]1[CH:12]=[C:11]([N:13]2[CH2:17][CH2:16][N:15]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][C:23]=3[CH3:24])[C:14]2=[O:25])[CH:10]=[CH:9][C:6]=1[C:7]#[N:8].CO>COCCO.C(Cl)(Cl)Cl>[NH2:8][C:7]1[C:6]2[C:5](=[CH:12][C:11]([N:13]3[CH2:17][CH2:16][N:15]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][C:23]=4[CH3:24])[C:14]3=[O:25])=[CH:10][CH:9]=2)[N:2]([CH3:1])[N:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 6061MethylhydrazineHCID 59636138HCID 59636138, compound

Product 1

HCID 59636156HCID 59636156, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
170 °C

Procedure

Methyl hydrazine (10 mL) was added to a stirred solution of 2-fluoro-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzonitrile (I-123a: 240 mg, 0.80998 mmol) in 2-methoxy ethanol (20 mL). The resulting mixture was stirred at 170° C. for 12 hours. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was cooled to room temperature and concentrated. Ice was added to the concentrate and the precipitate formed was collected and dried under reduced pressure to afford 180 mg of the product (69.2% yield).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. additionIce was added to the
  4. concentrationconcentrate
  5. customthe precipitate formed
  6. customwas collected
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-615523b41af642eb8dc8628952cb7eaf
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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