Water → 6-({2-[(7-Chloro[1,2,4]triazolo[1,5-c]pyrimidin-5-yl)amino]ethyl}amino)nicotinonitrile

HRID 2389767Notes

Reaction equation

Cl[C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([Cl:11])[N:3]=1.FC(F)(F)C(O)=O.[NH2:19][CH2:20][CH2:21][NH:22][C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][N:24]=1.CCN(C(C)C)C(C)C.O>CC(O)C>[Cl:11][C:4]1[N:3]=[C:2]([NH:19][CH2:20][CH2:21][NH:22][C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][N:24]=2)[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

707 mg (3.20 mmol) of 5,7-dichloroimidazo[1,2-c]pyrimidine (Example 53A) are suspended in 25 ml of 2-propanol, and 1.35 g (3.52 mmol) of 6-[(2-aminoethyl)amino]nicotinonitrile trifluoroacetate (Example 13A) and 1.03 g (7.99 mmol) of DIPEA are added. The mixture is heated at 80° C. for 16 h. After this time, water is added and the precipitate which separates out is filtered off with suction. It is washed with a little 2-propanol/water, and the resulting solid is dried under high vacuum. 523 mg (50% of theory) of the product is obtained as a solid.

Workup

filtrationthe precipitate which separates out is filtered off with suction
washIt is washed with a little 2-propanol/water
customthe resulting solid is dried under high vacuum
custom523 mg (50% of theory) of the product is obtained as a solid

Sources & evidence

ORD record: ord-d6b7b44918f64034af8880cd5719c21e
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273752B2

Reaction notes

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