Water → N6-{2-[(7-Chloro[1,2,4]triazolo[1,5-c]pyrimidin-5-yl)amino]ethyl}-3-nitropyridine-2,6-diamine

HRID 2171506Notes

Reaction equation

Cl[C:2]1[N:7]2C=[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[N:28]=[C:27]([NH2:29])[C:26]([N+:30]([O-:32])=[O:31])=[CH:25][CH:24]=1.CC[N:35](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[N:28]=[C:27]([NH2:29])[C:26]([N+:30]([O-:32])=[O:31])=[CH:25][CH:24]=2)[N:7]2[N:35]=[CH:9][N:10]=[C:6]2[CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

194 mg (3.20 mmol) of 5,7-dichloroimidazo[1,2-c]pyrimidine are suspended in 8 ml of 2-propanol, and 403.9 mg (1.13 mmol) of N6-(2-aminoethyl)-3-nitropyridine-2,6-diamine trifluoroacetate and 331.7 mg (2.57 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. 265 mg (74% of theory) of the product are 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
custom265 mg (74% of theory) of the product are obtained as a solid

Sources & evidence

ORD record: ord-42a64e053a5240c6bfabe5da8878180c
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051323B2

Reaction notes

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