Acetic Acid → HCID 178428391, compound

HRID 80207

Reaction equation

HRID 80207 reaction equation
C(O)(=O)C.[NH2:5][NH2:6].F[C:8]1[CH:9]=[C:10]([N:20]2[CH2:24][CH2:23][N:22]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][C:30]=3[CH3:31])[C:21]2=[O:32])[CH:11]=[CH:12][C:13]=1[C:14](=O)[C:15]([F:18])([F:17])[F:16].CO>C1COCC1.C(Cl)(Cl)Cl>[CH3:31][C:30]1[CH:29]=[CH:28][N:27]=[CH:26][C:25]=1[N:22]1[CH2:23][CH2:24][N:20]([C:10]2[CH:9]=[C:8]3[C:13]([C:14]([C:15]([F:18])([F:17])[F:16])=[N:5][NH:6]3)=[CH:12][CH:11]=2)[C:21]1=[O:32]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 9321HydrazineHCID 596361941-[3-Fluoro-4-(2,2,2-trifluoroacetyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

Product 1

HCID 178428391HCID 178428391, compoundYield 23.46%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
150 °C

Procedure

Acetic acid (0.1 mL, 1.36 mmol) and 1M hydrazine in THF (4 mL, 2.72 mmol) were added to 1-[3-fluoro-4-(2,2,2-trifluoro-acetyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-160b: 100 mg, 0.272 mmol) in dry THF (2 mL). The resulting mixture was stirred at 150° C. overnight. The reaction was monitored by TLC (5% MeOH in CHCl3). The reaction mixture was partitioned between water and chloroform. The organic layer was dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (4% MeOH in CHCl3), followed by preparative HPLC afforded 23 mg of the product (23.46% yield).

Workup

  1. customThe reaction mixture was partitioned between water and chloroform
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customPurification by column chromatography on silica gel (4% MeOH in CHCl3)

Sources & evidence

ORD record
ord-869e360651c84a5babc1fe50126179d8
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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