2,4-Dichloro-6-methoxy-3,5-triazine → HCID 86615299, compound

HRID 2264499Notes

Reaction equation

HRID 2264499 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][CH3:10])[N:3]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([NH2:24])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(C(C)C)C(C)C)C>C(#N)C>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([NH:24][C:2]2[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][CH3:10])[N:3]=2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 192672,4-Dichloro-6-methoxy-3,5-triazineHCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 86615299HCID 86615299, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2,4-dichloro-6-methoxy-1,3,5-triazine (10.0 g, 55.6 mmol, 1.0 equiv) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (11.4 g, 55.6 mmol, 1.0 equiv) in acetonitrile (300 mL) was added drop by drop N-ethyl diisopropylamine (48.5 mL, 36.6 g, 278 mmol, 5.0 equiv) keeping the temperature below 25° C. After stirring the reaction mixture at rt for 16 h, the heterogeneous mixture was poured onto ice water and extracted three times with ethyl acetate. The combined organic layers were washed with brine and water, dried over MgSO4, filtered and concentrated by evaporation under reduced pressure. The crude product was purified by column chromatography on silica eluting with a gradient of dichloromethane/methanol to give 11.4 g (60%) of the title compound as a off-white foam. MS (ISP): 344.3 [M+H]+.

Workup

  1. customthe temperature below 25° C
  2. additionthe heterogeneous mixture was poured onto ice water
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic layers were washed with brine and water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customThe crude product was purified by column chromatography on silica eluting with a gradient of dichloromethane/methanol

Sources & evidence

ORD record
ord-2bd9eff133fb44f2bd7e894266e3b561
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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