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

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	3-amino-N-(isopropyl)benzamide	HCID 3019023	—
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	4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4yl)-piperidine-4-carboxylic acid	HCID 67036781	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(3-(isopropylcarbamoyl)phenyl)-4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide	HCID 44478472	48.1%

Reaction Conditions

Temperature	50 °C

Reaction Steps

To a solution of 4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4yl)-piperidine-4-carboxylic acid from example 6, step B, (0.030 g, 0.11 mmol) in DMF (1 mL) were added HATU (0.042 g, 0.11 mmol), triethylamine (0.028 mL, 0.22 mmol) and 3-amino-N-isopropyl-benzamide (0.029 mg, 0.17 mmol). The reaction was stirred at 50° C. for 48 hours and concentrated under vacuum. The residue was purified by prep HPLC to give the title compound (0.023 g, 48%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08193202B2
Source dataset	uspto-grants-2012_06
ORD ID	ord-117ced0733d14ae293bdf0ce692966a2
Source note	uspto-grants-2012_06