Triacetoxyperiodinane → HCID 178457815, compound

HRID 518668Notes

Reaction equation

HRID 518668 reaction equation
[F:1][C:2]1[CH:35]=[CH:34][C:5]([C:6](/[N:8]=[C:9]2\[NH:10][C:11]3[N:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][OH:20])=[CH:13][C:12]=3[N:21]\2[C@H:22]2[CH2:27][CH2:26][C@@H:25]([C:28](=[O:33])[NH:29][CH:30]([CH3:32])[CH3:31])[CH2:24][CH2:23]2)=[O:7])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](/[N:8]=[C:9]2\[NH:10][C:11]3[N:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]=[O:20])=[CH:13][C:12]=3[N:21]\2[C@H:22]2[CH2:23][CH2:24][C@@H:25]([C:28](=[O:33])[NH:29][CH:30]([CH3:31])[CH3:32])[CH2:26][CH2:27]2)=[O:7])=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 178457816HCID 178457816, compound

Product 1

HCID 178457815HCID 178457815, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(E)-4-Fluoro-N-(6-(2-hydroxyethoxy)-1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-1H-imidazo[4,5-e]pyridin-2(3H)-ylidene)benzamide (0.043 g, 0.089 mmol) was suspended in DCM (3.56 mL) under nitrogen, and the reaction flask was cooled to 0° C. To the flask was added Dess-Martin periodinane (0.057 g, 0.133 mmol), and the reaction was allowed to warm to RT and stirred for 1 hour. The reaction was quenched with aqueous NaHCO3 (8 mL) and sodium thiosulfate (85 mg). The product was extracted with 5% MeOH/DCM. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford (E)-4-fluoro-N-(1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-6-(2-oxoethoxy)-1H-imidazo[4,5-e]pyridin-2(3H)-ylidene)benzamide as a light pink solid. MS m/z=482.0 [M+H], calc 481.52 for C25H28FN5O4.

Workup

  1. temperatureto warm to RT
  2. customThe reaction was quenched with aqueous NaHCO3 (8 mL) and sodium thiosulfate (85 mg)
  3. extractionThe product was extracted with 5% MeOH/DCM
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-78819449f8944fa2af339b6d0e368802
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

Loading…