Dichloromethane → tert-butyl 4-(3,3,7-trimethyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)piperidine-1-carboxylate

HRID 1026546Notes

Reaction equation

HRID 1026546 reaction equation
ClCCl.[OH:4][C:5]1[C:10]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[CH:9][C:8]([CH3:25])=[CH:7][N:6]=1.N1C(C)=CC=CC=1C.Br[C:35]([CH3:40])([CH3:39])[C:36](Br)=[O:37]>CN(C)C=O>[CH3:39][C:35]1([CH3:40])[O:4][C:5]2[N:6]=[CH:7][C:8]([CH3:25])=[CH:9][C:10]=2[N:11]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:14][CH2:13]2)[C:36]1=[O:37]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 79372,6-LutidineHCID 886852-Bromo-2-methylpropionyl bromideHCID 178430714HCID 178430714, compound

Product 1

HCID 68006021tert-butyl 4-(3,3,7-trimethyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At room temperature, to a dichloromethane solution (15 ml) of tert-butyl 4-[(2-hydroxy-5-methylpyridin-3-yl)amino]piperidine-1-carboxylate (3.08 g) were added 2,6-lutidine (2.25 ml) and 2-bromoisobutyryl bromide (1.74 ml). After stirring at room temperature for 18 hours, N,N-dimethylformamide (15 ml) was added, and stirred at 70° C. for 1 hour. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to afford tert-butyl 4-(3,3,7-trimethyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)piperidine-1-carboxylate (1.04 g).

Workup

  1. stirringstirred at 70° C. for 1 hour
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c1a5d52281a047dd95b8721513c6686a
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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