Diisopropylethylamine → HCID 67342449, compound

HRID 451511

Reaction equation

HRID 451511 reaction equation
IC1C=[CH:6][N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])C=1.[C:12]([N:19]1CCC(N)C[CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[CH3:26][CH2:27][N:28]([CH:32]([CH3:34])[CH3:33])[CH:29]([CH3:31])C>CN1C(=O)CCC1>[F:11][C:8]([F:9])([F:10])[C:4]1[CH:33]=[C:32]([N:28]2[CH2:27][CH2:26][CH:20]([NH:19][C:12](=[O:13])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:31][CH2:29]2)[CH:34]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 234369404-Iodo-2-(trifluoromethyl)pyridine

Product 1

HCID 67342449HCID 67342449, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a mixture of 4-iodo-2-(trifluoromethyl)pyridine (356 mg, 1.3 mmol) and Boc-4-aminopiperidine (340 mg, 1.7 mmol) in NMP (2.6 mL) was added DIPEA (319 L, 1.83 mmol). Argon was bubbled through the cloudy solution for 5 minutes before the reaction mixture was heated in the microwave for 3×30 minutes to 150° C. The mixture was then poured into water and extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and evaporated. Purification by chromatography (silica gel, 50 g, 0 to 100% ethyl acetate in heptane) afforded the title compound (343 mg, 76%) as a white solid.

Workup

  1. customArgon was bubbled through the cloudy solution for 5 minutes before the reaction mixture
  2. temperaturewas heated in the microwave for 3×30 minutes to 150° C
  3. additionThe mixture was then poured into water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by chromatography (silica gel, 50 g, 0 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-97a5cba06aba46a4b17d85304e4b67f4
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Linked notes

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