Methanol → HCID 49872353, compound

HRID 80158Notes

Reaction equation

HRID 80158 reaction equation
O.[NH2:2][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>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)[NH:3][N:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 59636138HCID 59636138, compound

Product 1

HCID 49872353HCID 49872353, compoundYield 17.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
170 °C

Procedure

Hydrazine hydrate (5 mL) was added to solution of 2-fluoro-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzonitrile (I-123a: 163 mg) in 2-methoxymethanol (10 mL). The resulting mixture was heated to 170° C. and maintained for 22 hours. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was partitioned between ice water and ethylacetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. Purification by preparative HPLC afforded 30 mg of the product (17.6% yield).

Workup

  1. temperaturemaintained for 22 hours
  2. customThe reaction mixture was partitioned between ice water and ethylacetate
  3. washThe organic layer was washed with brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-8c42f7b5f27e46f3ad64a137b43c884d
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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