Pyridine → HCID 81802526, compound

HRID 2179122Notes

Reaction equation

HRID 2179122 reaction equation
[CH3:1][NH:2][CH2:3][C:4]#[CH:5].N1C=CC=CC=1.[F:12][C:13]([F:24])([F:23])[C:14]1[N:19]=[CH:18][C:17]([C:20](Cl)=[O:21])=[CH:16][CH:15]=1>ClCCl>[CH3:1][N:2]([CH2:3][C:4]#[CH:5])[C:20](=[O:21])[C:17]1[CH:16]=[CH:15][C:14]([C:13]([F:24])([F:23])[F:12])=[N:19][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 96160N-methylpropyn-2-ylamineHCID 27775576-(Trifluoromethyl)nicotinoyl chloride

Product 1

HCID 81802526HCID 81802526, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-methylpropargylamine (95%, 1.0 g, 13.75 mmol) and pyridine (5 mL) in dry dichloromethane (DCM)(50 mL) were cooled with ice-water. 6-(Trifluoromethyl)pyridine-3-carbonyl chloride (97%, 2.83 g, 13.10 mmol) was added drop wise with a syringe. The ice bath was removed and the mixture was stirred at room temperature overnight. DCM (150 mL) was added and the mixture was washed with water (3×100 mL). The organic phase was dried with anhydrous MgSO4, filtered and evaporated to dryness, then purified by silica gel column chromatography, eluting with MeOH/DCM (0-2%) to give the product (1.96 g, 70.0% yield), LRMS ESI (M+H+) 243, HPLC rt=5.4 min.

Workup

  1. customThe ice bath was removed
  2. additionDCM (150 mL) was added
  3. washthe mixture was washed with water (3×100 mL)
  4. dry with materialThe organic phase was dried with anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. custompurified by silica gel column chromatography
  8. washeluting with MeOH/DCM (0-2%)

Sources & evidence

ORD record
ord-5537289fbe334b5586ad431a78de1160
Source dataset
uspto-grants-2015_06
Patent number
US09067963B2

Reaction notes

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