2-Bromo-5-nitrothiazole → N-[7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]-N'-(5-nitro-1,3-thiazol-2-yl)ethane-1,2-diamine

HRID 2171583Notes

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.Br[C:30]1[S:31][C:32]([N+:35]([O-:37])=[O:36])=[CH:33][N:34]=1.CCN(C(C)C)C(C)C>CS(C)=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][NH:25][C:30]2[S:31][C:32]([N+:35]([O-:37])=[O:36])=[CH:33][N:34]=2)[N:19]2[CH:26]=[CH:27][N:28]=[C:18]2[CH:17]=1

Participants

Conditions

Temperature: 130 °C

Procedure

100 mg (0.238 mmol) of the amine (Example 8A) are introduced into 3 ml of DMSO, 76 mg (0.357 mmol) of 2-bromo-5-nitro-1,3-thiazole and 154 mg (1.19 mmol) of DIEA are added, and the mixture is heated in a microwave at 130° C. for 30 min. Purification by preparative HPLC results in 35 mg (33% of theory) of the product as a solid.

Workup

additionare added
customPurification by preparative HPLC

Sources & evidence

ORD record: ord-0832e7db35b94d71a4310c0dd566c8c4
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051323B2

Reaction notes

Loading…