tert-butyl 4-({2-[(1S)-2-tert-butoxy-1-methyl-2-oxoethoxy]-5-fluoropyridin-3-yl}amino)piperidine-1-carboxylate → (3S)-7-fluoro-3-methyl-1-piperidin-4-yl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

HRID 1026537Notes

Reaction equation

HRID 1026537 reaction equation
C([O:5][C:6](=O)[C@H:7]([CH3:30])[O:8][C:9]1[C:14]([NH:15][CH:16]2[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]2)=[CH:13][C:12]([F:29])=[CH:11][N:10]=1)(C)(C)C>FC(F)(F)C(O)=O>[F:29][C:12]1[CH:11]=[N:10][C:9]2[O:8][C@@H:7]([CH3:30])[C:6](=[O:5])[N:15]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:14]=2[CH:13]=1

Participants

3

Reactant 1

HCID 68006246tert-butyl 4-({2-[(1S)-2-tert-butoxy-1-methyl-2-oxoethoxy]-5-fluoropyridin-3-yl}amino)piperidine-1-carboxylate

Product 1

HCID 68006437(3S)-7-fluoro-3-methyl-1-piperidin-4-yl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-oneYield 83.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A trifluoroacetic acid solution (10 ml) of tert-butyl 4-({2-[(1S)-2-tert-butoxy-1-methyl-2-oxoethoxy]-5-fluoropyridin-3-yl}amino)piperidine-1-carboxylate (861 mg) was stirred at room temperature for 24 hours, and then concentrated under reduced pressure. To the residue were added dichloromethane and a saturated aqueous sodium hydrogen carbonate solution, and the solution was separated. The aqueous layer was saturated with salt, and then extracted with dichloromethane. The collected organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford (3S)-7-fluoro-3-methyl-1-piperidin-4-yl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one (434 mg).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue were added dichloromethane
  3. customa saturated aqueous sodium hydrogen carbonate solution, and the solution was separated
  4. extractionextracted with dichloromethane
  5. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a648421cbcd447709dcf3bd73db61640
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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