Dimethyl Sulfoxide → 2-(3,5-bis(trifluoromethyl)phenyl)-N-(4-(2-chlorophenyl)-6-(2-hydroxyethylamino)pyridin-3-yl)-N,2-dimethylpropanamide

HRID 547760Notes

Reaction equation

HRID 547760 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C:13]([CH3:33])([CH3:32])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21](Cl)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CS(C)=O.[CH2:40]([CH2:42][NH2:43])[OH:41]>C(OCC)(=O)C>[F:11][C:9]([F:12])([F:10])[C:7]1[CH:6]=[C:5]([C:13]([CH3:32])([CH3:33])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([NH:43][CH2:42][CH2:40][OH:41])=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[CH3:17])=[O:15])[CH:4]=[C:3]([C:2]([F:1])([F:34])[F:35])[CH:8]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 700EthanolamineHCID 23502837HCID 23502837, compound

Product 1

HCID 103030992-(3,5-bis(trifluoromethyl)phenyl)-N-(4-(2-chlorophenyl)-6-(2-hydroxyethylamino)pyridin-3-yl)-N,2-dimethylpropanamideYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 28.6 g (56 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[6-chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide, 50 ml dimethyl sulfoxide and 50 ml (830 mmol) ethanolamine was stirred at 140° C. for 24 h. The reaction mixture was cooled to room temperature, diluted with 200 ml ethyl acetate and washed with 200 ml 1 N sodium carbonate solution and 100 ml water. The aqueous layers were extracted with two 200-ml portions of ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was crystallized from a mixture of 150 ml diisopropyl ether and 150 ml heptane to give 29.1 g (93%) of the title compound as white crystals. M.p. 117-118° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with 200 ml 1 N sodium carbonate solution and 100 ml water
  3. extractionThe aqueous layers were extracted with two 200-ml portions of ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from a mixture of 150 ml diisopropyl ether and 150 ml heptane

Sources & evidence

ORD record
ord-aa95914b3c254275a47d6b22f5a40a7a
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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