Diisopropylethylamine → 2-amino-N-(1-methyl-4-piperidyl)-1,3-thiazole-4-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-Amino-1-methylpiperidine	HCID 2737531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	2-Amino-4-thiazolecarboxylic acid hydrobromide	HCID 16217717	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-amino-N-(1-methyl-4-piperidyl)-1,3-thiazole-4-carboxamide	HCID 62789066	53%

Reaction Steps

2-Aminothiazole-4-carboxylate hydrobromide salt (Chempacific; 1.13 g, 5.02 mmol), HATU (2.87 g, 7.53 mmol) and 4-amino-1-methylpiperidine (0.86 g, 7.53 mmol) were stirred in DMF (5 mL) and DIPEA (5.2 mL, 30.12 mmol) added. The mixture was stirred at room temperature overnight. The reaction mixture was concentrated and the residue taken up in methanol, absorbed onto an SCX column, washed with methanol and eluted with ammonia in methanol. Product containing fractions were combined, evaporated and the residue and further purified by column chromatography (5% 7N NH3 in MeOH/DCM) Product containing fractions were combined and evaporated to give the title compound as a yellow solid (635 mg, 53%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07709471B2
Source dataset	uspto-grants-2010_05
ORD ID	ord-804b6f9d0a684bb2848bff3904e15ed0
Source note	uspto-grants-2010_05