Dimethyl Sulfoxide → 6-[(2-{[7-(2,4-Dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]amino}propyl)amino]-nicotinonitrile

HRID 2389831Notes

Reaction equation

FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[N:21]=[C:20]([NH:22][CH:23]([CH3:26])[CH2:24][NH2:25])[N:19]2[CH:27]=[CH:28][N:29]=[C:18]2[CH:17]=1.Cl[C:31]1[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][N:32]=1.C(N(CC)C(C)C)(C)C.CS(C)=O>O>[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[N:21]=[C:20]([NH:22][CH:23]([CH3:26])[CH2:24][NH:25][C:31]2[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][N:32]=2)[N:19]2[CH:27]=[CH:28][N:29]=[C:18]2[CH:17]=1

Participants

Conditions

Temperature: 150 °C

Procedure

The amine (Example 37A) (300 mg, 0.46 mmol), 2-chloro-5-cyanopyridine (129 mg, 0.93 mmol) and N,N-diisopropylethylamine (600 mg, 4.6 mmol) are introduced into DMSO (6 ml), and heated at 150° C. in a microwave oven for 30 min. The reaction mixture is poured into water and extracted with ethyl acetate (3×25 ml). The combined organic phases are washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated. The residue is taken up in acetonitrile, and the product precipitates and is washed with acetonitrile and dried. 87 mg (41% of theory) of the product are obtained as a solid.

Workup

extractionextracted with ethyl acetate (3×25 ml)
washThe combined organic phases are washed with saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulphate
concentrationconcentrated
customthe product precipitates
washis washed with acetonitrile
customdried
custom87 mg (41% of theory) of the product are obtained as a solid

Sources & evidence

ORD record: ord-6a8fc743475e4029b96a62c75989bfb4
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273752B2

Reaction notes

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