Ethanamine, 2,2,2-trifluoro- → 6-methyl-N-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-2-((2,2,2-trifluoroethyl)amino)pyrimidine-4-carboxamide

HRID 623657Notes

Reaction equation

HRID 623657 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([NH:10][CH:11]([C:13]2[CH:14]=[N:15][C:16]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:17][CH:18]=2)[CH3:12])=[O:9])[CH:5]=[C:4]([CH3:25])[N:3]=1.[F:26][C:27]([F:31])([F:30])[CH2:28][NH2:29]>>[CH3:25][C:4]1[N:3]=[C:2]([NH:29][CH2:28][C:27]([F:31])([F:30])[F:26])[N:7]=[C:6]([C:8]([NH:10][CH:11]([C:13]2[CH:14]=[N:15][C:16]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:17][CH:18]=2)[CH3:12])=[O:9])[CH:5]=1

Participants

3

Reactant 2

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 874270222-chloro-6-methyl-N-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)pyrimidine-4-carb oxamide

Product 1

HCID 874264976-methyl-N-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-2-((2,2,2-trifluoroethyl)amino)pyrimidine-4-carboxamideYield 12%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-6-methyl-N-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)pyrimidine-4-carb oxamide (50 mg, 0.13 mmol, Step-1 of Example 536, single enantiomer) and 2,2,2-trifluoroethanamine (3.5 mL) is heated at 100° C. for 4 days in a sealed tube. After cooled to room temperature, the mixture is concentrated and then purified by preparative LC-MS to give 7 mg (12% yield) of the title compound.

Workup

  1. temperatureAfter cooled to room temperature
  2. concentrationthe mixture is concentrated
  3. custompurified by preparative LC-MS

Sources & evidence

ORD record
ord-cf25859077684aeeb3cac04fe1dd0810
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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