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

HRID 2171485Notes

Reaction equation

Cl[C:2]1[N:7]2[CH: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[N:28]=[C:27]([NH2:29])[C:26]([N+:30]([O-:32])=[O:31])=[CH:25][CH:24]=1.CCN(C(C)C)C(C)C.O>CS(C)=O>[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[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=1

Participants

Conditions

Temperature: 120 °C

Procedure

800 mg (4.13 mmol) of 5,7-dichloroimidazo[1,2-c]pyrimidine (Example 11A) are suspended in 20 ml of DMSO, and 1.62 g (4.54 mmol) of N6-(2-aminoethyl)-3-nitropyridine-2,6-diamine trifluoroacetate (Example 15A) and 1.6 g (12.38 mmol) of DIPEA are added. The mixture is heated at 120° C. for 16 h. After this time, water is added, and the precipitate which has separated out is filtered off with suction. It is washed with a little 2-propanol/water and the resulting solid is dried under high vacuum. 1.34 g (92% of theory) of the product are obtained as a solid.

Workup

customthe precipitate which has separated out
filtrationis filtered off with suction
washIt is washed with a little 2-propanol/water
customthe resulting solid is dried under high vacuum
custom1.34 g (92% of theory) of the product are obtained as a solid

Sources & evidence

ORD record: ord-b1ad431128e64ac28c69167a5215e102
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051323B2

Reaction notes

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