4-(Aminomethyl)benzonitrile → 2-(4-cyanobenzylamino)-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide

HRID 715754Notes

Reaction equation

Br[C:2]1[S:3][C:4]([C:7]([NH:9][C:10]2[CH:11]=[CH:12][C:13]3[N:14]([CH:16]=[CH:17][N:18]=3)[CH:15]=2)=[O:8])=[CH:5][N:6]=1.[C:19]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=1)#[N:20]>C(#N)C>[C:19]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH:26][C:2]2[S:3][C:4]([C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]4[N:14]([CH:16]=[CH:17][N:18]=4)[CH:15]=3)=[O:8])=[CH:5][N:6]=2)=[CH:23][CH:22]=1)#[N:20]

Participants

Conditions

Temperature: 180 °C

Procedure

To a solution of 2-bromo-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide (165 mg, 0.511 mmol) in acetonitrile (2553 μl) was added 4-cyanobenzylamine (67.5 mg, 0.511 mmol). The mixture was heated in a microwave (Biotage Initiator) at 180° C. for 30 minutes. The heating was repeated again after another equivalent of 4-cyanobenzylamine was added. The reaction mixture was purified by normal phase chromatography to provide the title compound.

Workup

additionwas added
customThe reaction mixture was purified by normal phase chromatography

Sources & evidence

ORD record: ord-a659ded7c8e843c392355d07d0c7e6bd
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187472B2

Reaction notes

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