Triethylamine → HCID 68781393, compound

HRID 2264422Notes

Reaction equation

HRID 2264422 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][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(CC)CC)C>CN(C=O)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]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 27739122-Chloro-4-(trifluoromethyl)pyrimidine

Product 1

HCID 68781393HCID 68781393, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloro-4-trifluoromethyl-pyrimidine (2.15 g, 11.78 mmol, 1.0 equiv; commercially available) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (3.07 g, 15.31 mmol, 1.3 equiv; commercially available) in anhydrous DMF (15 mL) and triethylamine (5 mL) was heated to 100° C. for 3 h. The organic phase was concentrated under reduced pressure and the residue extracted with dichloromethane (3×50 mL) from a sat. solution of sodium bicarbonate (100 mL). The combined organic phases were dried over MgSO4 and the product purified with column chromatography on silica eluting with heptane/ethyl acetate (5:1+1% triethylamine) providing 3.47 g (85%) of the title compound. MS (ISP): 347.1 [M+H]+.

Workup

  1. concentrationThe organic phase was concentrated under reduced pressure
  2. extractionthe residue extracted with dichloromethane (3×50 mL) from a sat. solution of sodium bicarbonate (100 mL)
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. customthe product purified with column chromatography on silica eluting with heptane/ethyl acetate (5:1+1% triethylamine)

Sources & evidence

ORD record
ord-57264a18e9564fabac5774cf023685de
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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