Triethylamine → HCID 71522920, compound

HRID 2178543Notes

Reaction equation

HRID 2178543 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([CH:16]=[CH2:17])[C:6]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=[O:15])=[N:7][CH:8]=1.[NH:20]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[CH2:21]1.C(N(CC)CC)C>C(O)C>[N:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH:22]1[CH2:23][CH2:24][N:20]([CH2:17][CH2:16][C:5]2[C:6]([N:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]3=[O:15])=[N:7][CH:8]=[C:3]([C:2]([F:1])([F:18])[F:19])[CH:4]=2)[CH2:21]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 50139382-(Pyrrolidin-3-yl)pyridineHCID 89500375HCID 89500375, compound

Product 1

HCID 71522920HCID 71522920, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-[5-(trifluoromethyl)-3-vinylpyridin-2-yl]piperidin-2-one a18-2 (310 mg, 1.147 mmol, 1 eq) and 2-pyrrolidin-3-yl pyridine (221 mg, 1.491 mmol, 1.3 eq) in ethanol (10 ml) is added triethylamine (348 mg, 479 μl, 3.441 mmol, 3 eq). The reaction mixture is stirred at 90° C. for 7 hours, then heated overnight at 85° C. The reaction mixture is evaporated to dryness and retaken in dichloromethane. This organic phase is washed with aqueous NH4Cl (1 time), saturated aqueous NaHCO3 (2 times), then dried over MgSO4, filtered and evaporated to dryness. The residue obtained is purified by flash chromatography over silicagel (12 g; gradient: from dichloromethane/MeOH 100/0 to 94/6), dried under vacuum to afford 91.4 mg of 1-[3-{2-[3-(pyridin-2-yl)pyrrolidin-1-yl]ethyl}-5-(trifluoromethyl)pyridin-2-yl]piperidin-2-one 110.

Workup

  1. temperatureheated overnight at 85° C
  2. customThe reaction mixture is evaporated to dryness
  3. washThis organic phase is washed with aqueous NH4Cl (1 time), saturated aqueous NaHCO3 (2 times)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue obtained
  8. customis purified by flash chromatography over silicagel (12 g; gradient: from dichloromethane/MeOH 100/0 to 94/6)
  9. customdried under vacuum

Sources & evidence

ORD record
ord-bae01fa909424a919be7a1fd34791d02
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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