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

HRID 715754
Notes
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Reaction equation

HRID 715754 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 826084-(Aminomethyl)benzonitrile2×HCID 867019292-bromo-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide

Product 1

HCID 867019282-(4-cyanobenzylamino)-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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

  1. additionwas added
  2. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes