Ammonium formate → HCID 10317591, compound

HRID 855549Notes

Reaction equation

HRID 855549 reaction equation
[CH:1]1(/[CH:6]=[C:7](\[C:16]2[CH:17]=[N:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)/[C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])=O.[NH4+]>[Pd].CO>[CH:1]1([CH2:6][CH:7]([C:16]2[CH:17]=[N:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 11740328HCID 11740328, compound

Product 1

HCID 10317591HCID 10317591, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (E)-3-cyclopentyl-2-(6-methanesulfonylpyridin-3-yl)-N-thiazol-2-ylacrylamide (EXAMPLE 35, 500 mg, 1.3 mmol), ammonium formate (500 mg, 7.9 mmol), and 10% palladium on charcoal (50% H2O, 500 mg) in MeOH (20 mL) was stirred at 80° C. for 20 h. The solvent was removed in vacuo, then the residue was diluted with EtOAc and filtered through Celite. The filtrate was concentrated and once again diluted with EtOAc, filtered through Celite and concentrated. Purification of the crude product by column chromatography (EtOAc-n-C6H14, 3:7 to 1:1) afforded the title compound: δH (CDCl3): 1.05-1.22 (m, 2H), 1.40-1.85 (m, 7H), 1.95 (dt, 1H), 2.29 (dt, 1H), 3.21 (s, 3H), 3.82 (t, 1H), 7.09 (d, 1H), 7.53 (d, 1H), 8.06 (d, 2H), 8.58 (t, 1H); m/z (APCI+)=380 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with EtOAc
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated
  5. additiononce again diluted with EtOAc
  6. filtrationfiltered through Celite
  7. concentrationconcentrated
  8. customPurification of the crude product by column chromatography (EtOAc-n-C6H14, 3:7 to 1:1)

Sources & evidence

ORD record
ord-60d3408d16734d409315869e2cd85025
Source dataset
uspto-grants-2007_08
Patent number
US07262196B2

Reaction notes

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