Dimethylformamide → 3-({4-[1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl]-5-methoxypyrimidin-2-yl}amino)-N-(tetrahydro-2H-pyran-4-yl)benzamide

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate	HCID 151348	—
Reactant	4-Aminotetrahydropyran	HCID 419223	—
Reactant	3-({4-[1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl]-5-methoxypyrimidin-2-yl}amino)benzoic Acid	HCID 68758597	—
Product	3-({4-[1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl]-5-methoxypyrimidin-2-yl}amino)-N-(tetrahydro-2H-pyran-4-yl)benzamide	HCID 58014385	—

Reaction Steps

To a mixture of 3-({4-[1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl]-5-methoxypyrimidin-2-yl}amino)benzoic acid (30 mg, 0.00007 mol), tetrahydro-2H-pyran-4-amine (7.5 mg, 0.000074 mol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (39 mg, 0.000089 mol) in N,N-dimethylformamide (0.5 mL, 0.006 mol) was added N,N-diisopropylethylamine (31 μL, 0.00018 mol). The reaction was stirred at room temperature for 1 h, quenched with water, purified on HPLC to give the desired product as a diastereomeric mixture (free base). LCMS (M+H) 488.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08309718B2
Source dataset	uspto-grants-2012_11
ORD ID	ord-22b45a19b5a5414192404e505a0cd067
Source note	uspto-grants-2012_11