2-Chloro-4,6-dimethoxy-1,3,5-triazine → HCID 68783648, compound

HRID 2264464Notes

Reaction equation

HRID 2264464 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([O:10][CH3:11])[N:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([NH2:25])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>C(#N)C>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([NH:25][C:2]2[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([O:10][CH3:11])[N:3]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 68783648HCID 68783648, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-chloro-4,6-dimethoxy-[1,3,5]triazine (1.35 g, 7.68 mmol, 1.0 equiv; commercially available) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (2.00 g, 9.98 mmol, 1.3 equiv; commercially available) in acetonitrile (16 mL) was heated by microwave irradiation to 160° C. for 20 min. The organic phase was concentrated under reduced pressure and the residue extracted with ethyl acetate (3×50 mL) from a solution of 1 M NaOH (200 mL). The combined organic phases were dried over MgSO4 and concentrated by evaporation under reduced pressure yielding 2.60 g (100%) of the title compound. MS (ISP): 340.4 [M+H]+.

Workup

  1. concentrationThe organic phase was concentrated under reduced pressure
  2. extractionthe residue extracted with ethyl acetate (3×50 mL) from a solution of 1 M NaOH (200 mL)
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-d7e7cca316704b869d288407628e28bd
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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