2-(Methylamino)ethanol → 2-(3,5-Bis-trifluoromethyl-phenyl)-N-{4-(4-fluoro-phenyl)-6-[(2-hydroxy-ethyl)-methyl-amino]-pyridin-3-yl}-N-methyl-isobutyramide

HRID 547770Notes

Reaction equation

HRID 547770 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][C:27]([F:30])=[CH:26][CH:25]=2)[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:36][NH:37][CH2:38][CH2:39][OH:40]>>[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]([N:37]([CH2:38][CH2:39][OH:40])[CH3:36])=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

3

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 235027832-(3,5-bis-trifluoromethyl-phenyl)-N-[6-chloro-4-(4-fluoro-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide

Product 1

HCID 865976802-(3,5-Bis-trifluoromethyl-phenyl)-N-{4-(4-fluoro-phenyl)-6-[(2-hydroxy-ethyl)-methyl-amino]-pyridin-3-yl}-N-methyl-isobutyramideYield 78%

Conditions

Temperature
140 °C

Procedure

A mixture of 0.10 g (0.20 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[6-chloro-4-(4-fluoro-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide and 0.45 g (6.0 mmol) 2-(methylamino)ethanol was stirred 6 h at 140° C. After cooling to room temperature the reaction mixture was partitioned between water and tert-butyl methyl ether and extracted with three portions of tert-butyl methyl ether. The combined organic extracts were washed with a saturated aqueous solution of ammonium chloride and water, dried over sodium sulfate and concentrated in vacuo. Flash column chromatography gave 87 mg (78%) of the title compound as a light yellow solid.

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. customwas partitioned between water and tert-butyl methyl ether
  3. extractionextracted with three portions of tert-butyl methyl ether
  4. washThe combined organic extracts were washed with a saturated aqueous solution of ammonium chloride and water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b5394efd1074ed78a23b3af29827266
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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