Dimethyl Sulfoxide → 6-[(2-{[7-(2,4-Dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]amino}propyl)amino]-nicotinonitrile
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]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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-eada09de620e42bbb97faa7a0fd94b5c
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09051323B2
Reaction notes
Loading…