Diisopropylethylamine → 1-(4-Fluoro-phenyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylicacid{6-[3-(4-methoxy-benzyl)-2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-5-yloxy]-1-methyl-1H-indazol-3-yl}-amide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid	HCID 21081527	—
Reactant	5-[(3-amino-1-methyl-1H-indazol-6-yl)oxy]-3-(4-methoxybenzyl)-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-one	HCID 70497185	—
Solvent	Dimethylformamide	HCID 6228	—
Product	1-(4-Fluoro-phenyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylicacid{6-[3-(4-methoxy-benzyl)-2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-5-yloxy]-1-methyl-1H-indazol-3-yl}-amide	HCID 70497011	18.9%

Reaction Steps

A solution of compound 276 (100.00 mg; 0.23 mmol; 1.00 eq.), 1-(4-fluoro-phenyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid (59.59 mg; 0.26 mmol; 1.10 eq.), pybop (157.16 mg; 0.30 mmol; 1.30 eq.), DMF (4.00 ml), and N,N-diisopropylethylamine (115.48 μl; 0.70 mmol; 3.00 eq.) was stirred at room temperature for 22 hours. The reaction was concentrated, redissolved in DMSO and purified via prep HPLC to afford 28 mg (16%) of 278 as an off-white solid. LC-MS (M+H=646, obsd.=646).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08569295B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-960bf076f7164f78a12e13d238483ec2
Source note	uspto-grants-2013_10