HCID 67246795, compound → HCID 59272361, compound

HRID 1970271Notes

Reaction equation

HRID 1970271 reaction equation
[CH3:1][O:2][C:3]([CH3:32])([CH3:31])[C:4]#[C:5][C:6]1[CH:7]=[C:8]2[C:19]3([CH2:23][O:22][C:21]([NH2:24])=[N:20]3)[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)[CH:17]=3)[O:12][C:9]2=[CH:10][CH:11]=1.[H][H]>[Pd].C(CC(OC)=O)C>[CH3:1][O:2][C:3]([CH3:32])([CH3:31])[CH2:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:19]3([CH2:23][O:22][C:21]([NH2:24])=[N:20]3)[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)[CH:17]=3)[O:12][C:9]2=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 67246795HCID 67246795, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 59272361HCID 59272361, compoundYield 49.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 12180Methyl butyrateSolvent

Procedure

To a solution of 7-(3-methoxy-3-methylbut-1-ynyl)-3-(pyridin-3-yl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine (110 mg, 0.258 mmol) in 1:1 methanol ethyl acetate (10 mL) was added Pd/C (5%) (274 mg, 2.58 mmol). The resulting slurry was maintained under 1 atm of hydrogen gas for 4 hours at which point another loading of Pd/C (5%) (274 mg, 2.58 mmol) was added and the reaction was maintained under 1 atm of hydrogen gas for an additional 3 hours. The reaction was filtered through a pad of celite, washing well with methanol and ethyl acetate. The derived mixture was filtered through a 0.1 micron frit and concentrated to provide 7-(3-methoxy-3-methylbutyl)-3-(3-pyridinyl)spiro[chromeno[2,3-b]pyridine-5,4′-[1,3]oxazol]-2′-amine (55 mg, 0.128 mmol, 49.5% yield) as a light yellow solid. MS m/z=431.2 [M+H]+. Calc'd for C25H27N4O3: 431.2.

Workup

  1. additionwas added
  2. filtrationThe reaction was filtered through a pad of celite
  3. washwashing well with methanol and ethyl acetate
  4. filtrationThe derived mixture was filtered through a 0.1 micron frit
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d29fe7c57fed46b6b08ffcf4353a5d6b
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

Loading…