HCID 68542324, compound → HCID 68548445, compound

HRID 2242898Notes

Reaction equation

HRID 2242898 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][C:17]2[N:18]=[C:19]([NH2:31])[C:20]3[N:21]([N:23]=[C:24]([C:26]4[O:27][CH:28]=[CH:29][CH:30]=4)[N:25]=3)[CH:22]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([NH2:31])[C:20]3[N:21]([N:23]=[C:24]([C:26]4[O:27][CH:28]=[CH:29][CH:30]=4)[N:25]=3)[CH:22]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 68542324HCID 68542324, compound

Product 1

HCID 68548445HCID 68548445, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 4-[3-(8-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-prop-2-ynyl]-piperazine-1-carboxylic acid tert-butyl ester (20 mg; see Example 12 above) in EtOH (1 mL) was added palladium (10 wt.% on activated carbon, ca. 5 mg). The reaction mixture was hydrogenated (45 psi) overnight, filtered through Celite and concentrated in vacuo. The resulting oil was purified by radial chromatography using 5% MeOH/CH2Cl2as eluent to afford the title compound. 1H NMR (400 MHz, CDCl3) δ 1.45 (s, 9H), 1.94 (m, 2H), 2.44 (m, 4H), 2.65 (t, 2H), 3.45 (m, 4H), 5.67 (s, 2H), 6.57 (dd, 1H), 7.13 (dd, 1H), 7.60 (s, 1H), 7.76 (s, 1H).

Workup

  1. custom(45 psi) overnight
  2. filtrationfiltered through Celite
  3. concentrationconcentrated in vacuo
  4. customThe resulting oil was purified by radial chromatography

Sources & evidence

ORD record
ord-fe2c95eb7fcf468aac7ebc3a48db557a
Source dataset
uspto-grants-2010_03
Patent number
US07674791B2

Reaction notes

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