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

HRID 2389822Notes

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][CH2:23][CH2:24][NH2:25])[N:19]2[CH:26]=[CH:27][N:28]=[C:18]2[CH:17]=1.Cl[C:30]1[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][N:31]=1.CCN(C(C)C)C(C)C>C(O)(C)C>[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][CH2:23][CH2:24][NH:25][C:30]2[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][N:31]=2)[N:19]2[CH:26]=[CH:27][N:28]=[C:18]2[CH:17]=1

Participants

Conditions

Temperature: 150 °C

Procedure

50 mg (0.155 mmol) of the amine (Example 8A) are introduced into 2 ml of isopropanol, 32.3 mg (0.233 mmol) of 6-chloronicotinonitrile and 30.09 mg (0.233 mmol) of DIPEA are added, and the mixture is heated in a microwave at 150° C. for 1 h. Purification by preparative HPLC results in 47 mg (71% of theory) of the product.

Workup

additionare added
customPurification by preparative HPLC
customresults in 47 mg (71% of theory) of the product

Sources & evidence

ORD record: ord-8c76d81e643f4a79a57003329edcc6ae
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273752B2

Reaction notes

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