Ethanolamine → N-(3,5-Bis-trifluoromethyl-benzyl)-6-(2-hydroxy-ethylamino)-N-methyl-4-o-tolyl-nicotinamide

HRID 1168318Notes

Reaction equation

HRID 1168318 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8](=[O:23])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12](Cl)=[N:11][CH:10]=1.[CH2:34]([CH2:36][NH2:37])[OH:35]>>[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8](=[O:23])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([NH:37][CH2:36][CH2:34][OH:35])=[N:11][CH:10]=1

Participants

3

Reactant 2

HCID 700Ethanolamine2×HCID 10277890N-(3,5-bis-trifluoromethyl-benzyl)-6-chloro-N-methyl-4-o-tolyl-nicotinamide

Product 1

HCID 10142310N-(3,5-Bis-trifluoromethyl-benzyl)-6-(2-hydroxy-ethylamino)-N-methyl-4-o-tolyl-nicotinamideYield 73.9%

Conditions

Temperature
100 °C

Procedure

A mixture of 0.837 g (1.72 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-chloro-N-methyl-4-o-tolyl-nicotinamide and 5.0 ml (83 mmol) ethanolamine was stirred at 100° C. for 48 h. After cooling to room temperature excess ethanolamine was removed under reduced pressure. The residue was dissolved in a mixture of ethyl acetate and saturated aqueous sodium bicarbonate solution. The layers were separated and the aqueous layer was extracted with two portions of ethyl acetate. The combined organic extracts were washed with saturated aqueous sodium bicarbonate solution and water, dried with sodium sulfate and concentrated to give 0.8 g of crude product. Flash chromatography afforded 0.650 g (73.9%) of the title compound as a white solid. MS m/e (%): 512 (M+H+, 100).

Workup

  1. customwas removed under reduced pressure
  2. dissolutionThe residue was dissolved in a mixture of ethyl acetate and saturated aqueous sodium bicarbonate solution
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with two portions of ethyl acetate
  5. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate solution and water
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated
  8. customto give 0.8 g of crude product

Sources & evidence

ORD record
ord-6b553dab5ce54ec3bd79ab42ef655eba
Source dataset
uspto-grants-2003_09
Patent number
US06624176B2

Reaction notes

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