Isopropanol → N-(3-(1H-tetrazol-5-yl)phenyl)-4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Isopropanol	HCID 3776	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-Chloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidine	HCID 14809282	—
Reactant	HCID 178431740	HCID 178431740	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	N-(3-(1H-tetrazol-5-yl)phenyl)-4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide	HCID 178430821	4.3%

Reaction Conditions

Temperature	105 °C

Reaction Steps

N-(3-(1H-tetrazol-5-yl)phenyl)-4-methylpiperidine-4-carboxamide from step B (93 mg, 0.29 mmol), 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (49 mg, 0.29 mmol), N,N-diisopropylethylamine (0.19 g. 1.45 mmol), isopropanol (4.0 mL), and DMSO (0.5 mL) were combined in a pressure rated sealed tube and heated at 105° C. for 18 hours. The mixture was concentrated, and the residue was purified by preprative HPLC to give the title compound in 4.3% yield.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08193202B2
Source dataset	uspto-grants-2012_06
ORD ID	ord-7a4525fcaad74211989a71c4ee2dc492
Source note	uspto-grants-2012_06