HCID 11303601, compound → HCID 11315118, compound

HRID 2242919Notes

Reaction equation

HRID 2242919 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[N:15]=[C:16]([NH2:28])[C:17]3[N:18]([N:20]=[C:21]([C:23]4[O:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)[CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[N:15]=[C:16]([NH2:28])[C:17]3[N:18]([N:20]=[C:21]([C:23]4[O:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)[CH:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 11303601HCID 11303601, compound

Product 1

HCID 11315118HCID 11315118, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(8-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (50 mg, 0.13 mmol; see Example 28 above) in MeOH (1 mL) was added palladium (10 wt.% on activated carbon, 10 mg). The reaction mixture was stirred at room temperature under hydrogen atmosphere (1 atm) for overnight. The reaction mixture was filtered through Celite and the filtrate was concentrated to yield title compound (2.5 mg, 5%) as yellow solid. 1H NMR (300 MHz, DMSO) δ 8.01 (br s, 1H), 7.89 (s, 1H), 7.47 (s, 2H), 7.09 (br s, 1 H), 6.69 (br s, 1H), 4.06 (d, J=11.7 Hz, 2H), 2.80-2.63 (m, 3H), 1.84-1.80 (m, 2H), 1.69-1.64 (m, 2H), 1.41 (s, 9 H). MS m/z=385 amu (M++H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c5cd329f96a44f0f8829ceab2d95d2c6
Source dataset
uspto-grants-2010_03
Patent number
US07674791B2

Reaction notes

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