Diisopropylethylamine → Ethyl 5-({2-[(5-cyanopyridin-2-yl)amino]ethyl}amino)-7-[4-(trifluoromethyl)phenyl][1,2,4]-triazolo[1,5-c]pyrimidine-2-carboxylate

HRID 2171587Notes

Reaction equation

HRID 2171587 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=[C:6]2[CH:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[N:3]=1.FC(F)(F)C(O)=O.[NH2:33][CH2:34][CH2:35][NH:36][C:37]1[CH:44]=[CH:43][C:40]([C:41]#[N:42])=[CH:39][N:38]=1.CCN(C(C)C)C(C)C>CS(C)=O>[C:41]([C:40]1[CH:43]=[CH:44][C:37]([NH:36][CH2:35][CH2:34][NH:33][C:2]2[N:7]3[N:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=[C:6]3[CH:5]=[C:4]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[N:3]=2)=[N:38][CH:39]=1)#[N:42]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 59313005HCID 59313005, compoundHCID 687096656-[(2-Aminoethyl)amino]nicotinonitrile trifluoroacetate

Product 1

HCID 59313130Ethyl 5-({2-[(5-cyanopyridin-2-yl)amino]ethyl}amino)-7-[4-(trifluoromethyl)phenyl][1,2,4]-triazolo[1,5-c]pyrimidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

200 mg (0.52 mmol) of ethyl 5-chloro-7-(4-trifluoromethylphenyl)[1,2,4]triazolo[1,5-c]pyrimidine-2-carboxylate (Example 149A) and 123 mg (0.62 mmol) of 6-[(2-aminoethyl)amino]pyridine-3-carbonitrile (Example 13A) are introduced into DMSO (2 ml), 0.54 ml (3.1 mmol) of DIEA is added, and the reaction solution is irradiated in a microwave reactor at 90° C. for 30 min. The reaction mixture is purified by preparative HPLC. 98 mg (38% of theory) of the product are obtained as a solid.

Workup

  1. additionis added
  2. customthe reaction solution is irradiated in a microwave reactor at 90° C. for 30 min
  3. customThe reaction mixture is purified by preparative HPLC
  4. custom98 mg (38% of theory) of the product are obtained as a solid

Sources & evidence

ORD record
ord-55cc2ba5baab4426a2ab7d43c92cca1a
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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