Diisopropylethylamine → 6-[(2-{[7-(2,4-Dichlorophenyl)-2-(morpholin-4-ylmethyl)[1,2,4]triazolo[1,5-c]pyrimidin-5-yl]-amino}ethyl)amino]pyridine-3-carbonitrile

HRID 2389853Notes

Reaction equation

HRID 2389853 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([CH2:11][N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[N:10]=[C:6]2[CH:5]=[C:4]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[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>[Cl:25][C:19]1[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=1[C:4]1[N:3]=[C:2]([NH:33][CH2:34][CH2:35][NH:36][C:37]2[N:38]=[CH:39][C:40]([C:41]#[N:42])=[CH:43][CH:44]=2)[N:7]2[N:8]=[C:9]([CH2:11][N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[N:10]=[C:6]2[CH:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 593131065-Chloro-7-(2,4-dichlorophenyl)-2-(morpholin-4-ylmethyl)[1,2,4]triazolo[1,5-c]pyrimidineHCID 687096656-[(2-Aminoethyl)amino]nicotinonitrile trifluoroacetate

Product 1

HCID 593131246-[(2-{[7-(2,4-Dichlorophenyl)-2-(morpholin-4-ylmethyl)[1,2,4]triazolo[1,5-c]pyrimidin-5-yl]-amino}ethyl)amino]pyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

100 mg (0.25 mmol) of 5-chloro-7-(2,4-dichlorophenyl)-2-(morpholin-4-ylmethyl)[1,2,4]-triazolo[1,5-c]pyrimidine (Example 150A) and 60 mg (0.30 mmol) of 6-[(2-aminoethyl)amino]pyridine-3-carbonitrile (Example 13A) are introduced into DMSO (4 ml), 0.26 ml (1.5 mmol) of DIEA is added, and the reaction solution is irradiated in a microwave reactor at 140° C. for 45 min. The reaction mixture is purified by preparative HPLC. 62 mg (46% 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 140° C. for 45 min
  3. customThe reaction mixture is purified by preparative HPLC
  4. custom62 mg (46% of theory) of the product are obtained as a solid

Sources & evidence

ORD record
ord-360d6c7429b0448c8ca718d040ff664b
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

Loading…