Diisopropylethylamine → HCID 67342990, compound

HRID 451502Notes

Reaction equation

HRID 451502 reaction equation
ClC1C=[C:4]([CH3:8])[N:5]=[N:6]C=1.[C:9]([N:16]1CCC(N)C[CH2:17]1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[CH3:23][CH2:24][N:25]([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])C>CN1C(=O)CCC1>[CH3:8][C:4]1[N:5]=[N:6][CH:30]=[C:29]([N:25]2[CH2:24][CH2:23][CH:17]([NH:16][C:9](=[O:10])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:28][CH2:26]2)[CH:31]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 19791860HCID 19791860, compound

Product 1

HCID 67342990HCID 67342990, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a mixture of 5-chloro-3-methylpyridazine (1.3 g, 10.1 mmol) and Boc-4-aminopiperidine (2.63 g, 13.1 mmol) in NMP (13 mL) was added DIPEA (2.47 mL, 14.2 mmol). Argon was bubbled through the cloudy solution for 5 minutes before the reaction mixture was heated in the microwave for 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, 50 to 100% ethyl acetate in heptane) afforded the title compound (2.18 g, 74%) as an off 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 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, 50 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-b87a0c2eb5ff4d4f9adaffb878d0364e
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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