HCID 57635145, compound → HCID 57635271, compound

HRID 1971111Notes

Reaction equation

HRID 1971111 reaction equation
[C:1]1([C:6]2[N:10]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:9]3=[C:8]([C:16]([NH:18][C@@H:19]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:20]([NH:22][CH3:23])=[O:21])=[O:17])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1>[Pd].CO>[CH:1]1([C:6]2[N:10]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:9]3=[C:8]([C:16]([NH:18][C@@H:19]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:20]([NH:22][CH3:23])=[O:21])=[O:17])[N:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 57635145HCID 57635145, compound

Product 1

HCID 57635271HCID 57635271, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent3×

Procedure

Palladium on carbon (wet) (0.014 mg, 0.013 mmol) was suspended in methanol (1 mL) and transferred under nitrogen into a hydrogenation reaction vessel followed by methanol (1 mL). (S)-3-cyclopentenyl-N-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-7-methyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxamide (0.062 g, 0.17 mmol) in methanol (3 mL) was added and the mixture was hydrogenated at 60 psi for 2 h. The mixture was filtered through a celite plug and concentrated. The residue was purified ion exchange chromatography, eluting the product with 2N methanolic ammonia to provide Compound 303 (0.05 mg, 78%) as a yellow solid. 1H-NMR (400 MHz, CDCl3) δ: 1.01 (s, 9H), 1.55 (m, 2H), 1.76 (m, 2H), 1.87 (m, 2H), 2.39 (s, 3H), 2.69 (m, 5H), 2.90 (s, 1H), 3.84 (m, 4H), 4.28 (s, 1H), 6.40 (m, 1H), 7.59 (d, 1H). LCMS (+ESI) m/z 376.2 [M+H]+.

Workup

  1. customtransferred under nitrogen into a hydrogenation reaction vessel
  2. filtrationThe mixture was filtered through a celite plug
  3. concentrationconcentrated
  4. customThe residue was purified ion exchange chromatography
  5. washeluting the product with 2N methanolic ammonia

Sources & evidence

ORD record
ord-a2e60e36f3994943a9e522942657166a
Source dataset
uspto-grants-2013_04
Patent number
US08431565B2

Reaction notes

Loading…