Acetic Anhydride → 1-(4-Cyclopropyl-2-hydroxypyridin-3-yl)-3-(2-(trifluoromethyl) pyridin-4-yl) imidazolidin-2-one

HRID 523614Notes

Reaction equation

HRID 523614 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][N+:7]([O-])=[CH:6][C:5]=2[N:11]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)[C:12]2=[O:26])[CH2:3][CH2:2]1.C(OC(=O)C)(=[O:29])C>>[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[C:6]([OH:29])[C:5]=2[N:11]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)[C:12]2=[O:26])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 710079694-Cyclopropyl-3-(2-oxo-3-(2-(trifluoromethyl) pyridin-4-yl)imidazolidin-1-yl) pyridine 1-oxide

Product 1

HCID 1785173291-(4-Cyclopropyl-2-hydroxypyridin-3-yl)-3-(2-(trifluoromethyl) pyridin-4-yl) imidazolidin-2-oneYield 8%

Procedure

4-Cyclopropyl-3-(2-oxo-3-(2-(trifluoromethyl)pyridin-4-yl)imidazolidin-1-yl)pyridine 1-oxide (I-50b: 100 mg, 0.273 mmol) was heated with acetic anhydride (5 mL) at 120° C. for 3 hours. The resulting mixture was concentrated, basified with dilute sodium bicarbonate solution, and diluted with DCM. The organic layer was dried over sodium sulphate and concentrated to afford the crude product. Purification by column chromatography on silica gel (3% methanol in chloroform), followed by preparative HPLC afforded 8 mg of the product (8% yield).

Workup

  1. concentrationThe resulting mixture was concentrated
  2. additiondiluted with DCM
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated
  5. customto afford the crude product
  6. customPurification by column chromatography on silica gel (3% methanol in chloroform)

Sources & evidence

ORD record
ord-1b51690ddca845549b0d5644b4074aa1
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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