(S)-3-(3,3-dimethylbut-1-ynyl)-7-(pyridin-3-yl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-2'-amine → (S)-3-(3,3-dimethylbutyl)-7-(pyridin-3-yl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-2'-amine

HRID 1970303Notes

Reaction equation

HRID 1970303 reaction equation
[CH3:1][C:2]([CH3:31])([CH3:30])[C:3]#[C:4][C:5]1[CH:6]=[C:7]2[C@:18]3([CH2:22][O:21][C:20]([NH2:23])=[N:19]3)[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)[CH:16]=3)[O:11][C:8]2=[N:9][CH:10]=1>CO.[Pd]>[CH3:1][C:2]([CH3:31])([CH3:30])[CH2:3][CH2:4][C:5]1[CH:6]=[C:7]2[C@:18]3([CH2:22][O:21][C:20]([NH2:23])=[N:19]3)[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)[CH:16]=3)[O:11][C:8]2=[N:9][CH:10]=1

Participants

4

Reactant 1

HCID 45256651(S)-3-(3,3-dimethylbut-1-ynyl)-7-(pyridin-3-yl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-2'-amine

Product 1

HCID 58466148(S)-3-(3,3-dimethylbutyl)-7-(pyridin-3-yl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-2'-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-3-(3,3-dimethylbut-1-ynyl)-7-(pyridin-3-yl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine (60 mg, 0.146 mmol) in 5 mL of methanol was added Pd/C (5%) (156 mg, 1.462 mmol). The mixture was maintained under an atmosphere of hydrogen gas for 20 hours before being filtered through a celite plug, washing well with methanol. The filtrate was concentrated and the derived residue was purified by silical gel chromatography (12 g, 0-10% methanol in methylenechloride with 0.1% ammonium hydroxide) to provide (S)-3-(3,3-dimethylbutyl)-7-(pyridin-3-yl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine as a white solid.

Workup

  1. temperatureThe mixture was maintained under an atmosphere of hydrogen gas for 20 hours
  2. filtrationbefore being filtered through a celite plug
  3. washwashing well with methanol
  4. concentrationThe filtrate was concentrated
  5. customthe derived residue was purified by silical gel chromatography (12 g, 0-10% methanol in methylenechloride with 0.1% ammonium hydroxide)

Sources & evidence

ORD record
ord-d0855102ef5043c991f3043b9ac0871f
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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