Ethanamine, 2,2,2-trifluoro- → HCID 68763991, compound

HRID 1968330Notes

Reaction equation

HRID 1968330 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([S:22][CH2:23][C:24]2[N:25]=[C:26]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[S:27][CH:28]=2)[N:3]=1.[F:36][C:37]([F:41])([F:40])[CH2:38][NH2:39]>O1CCCC1>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([C:26]2[S:27][CH:28]=[C:24]([CH2:23][S:22][C:4]3[C:5]([C:20]#[N:21])=[C:6]([C:10]4[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:14][CH:15]=4)[C:7]([C:8]#[N:9])=[C:2]([NH:39][CH2:38][C:37]([F:41])([F:40])[F:36])[N:3]=3)[N:25]=2)=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 9773Ethanamine, 2,2,2-trifluoro-3×HCID 866438472-Chloro-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-4-(4-(2-hydroxyethoxy)phenyl)pyridine-3,5-dicarbonitrile

Product 1

HCID 68763991HCID 68763991, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

140 mg (0.260 mmol) of 2-chloro-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-4-(4-(2-hydroxyethoxy)phenyl)pyridine-3,5-dicarbonitrile (Example 2A) and 52 mg (0.519 mmol) of 2,2,2-trifluoro-1-aminoethane were dissolved in 2 ml of tetrahydrofuran and stirred at room temperature overnight. A further 52 mg (0.519 mmol) of 2,2,2-trifluoro-1-aminoethane were added and stirring was continued for 6 hours, after which the reaction mixture was heated to 50° C. and stirred at this temperature overnight. A further 52 mg (0.519 mmol) of 2,2,2-trifluoro-1-aminoethane were added. The mixture was then stirred initially at 50° C. for 2 hours and then under reflux for four hours. Without further work-up, the reaction mixture was purified by preparative HPLC. 36 mg (yield: 23%) of the target compound were obtained.

Workup

  1. stirringstirring
  2. waitwas continued for 6 hours
  3. temperatureafter which the reaction mixture was heated to 50° C.
  4. stirringstirred at this temperature overnight
  5. stirringThe mixture was then stirred initially at 50° C. for 2 hours
  6. temperatureunder reflux for four hours
  7. customWithout further work-up, the reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-e0336e3e2c5242328b1cc3c52c06e01f
Source dataset
uspto-grants-2013_04
Patent number
US08420825B2

Reaction notes

Loading…