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

HRID 717914
Notes
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Reaction equation

HRID 717914 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-7808fe2db28646369c11ea9b9ce15b6f
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09193723B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes