Diisopropylethylamine → HCID 59200050, compound

https://huagongshe.com/reaction/2382084

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
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-(3-Fluorophenyl)-4-methylpyrimidine-5-carboxylic acid	HCID 61702587	—
Reactant	HCID 68554208	HCID 68554208	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 59200050	HCID 59200050	39.7%

Reaction Steps

A mixture of 3-ethyl-pyrrolo[2,3-c]pyridin-1-ylamine (93 mg, 0.577 mmol), 2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (134 mg, 0.757 mmol), HATU (263 mg, 0.692 mmol) and DIPEA (223 mg, 1.73 mmol) in DMF (3 mL) is heated at 1500 C. for 1 h. The reaction is quenched with water and extracted with EtOAc. The organic layer is dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography eluting with 0-100% ethyl acetate in heptane to afford 2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-ethyl-pyrrolo[2,3-c]pyridin-1-yl)-amide (86 mg). MS: 376 (M+H); 1H NMR (300 MHz, CD3OD): δ 9.15 (s, 1H), 8.69 (s, 1H), 8.37 (d, 1H), 8.15-8.26 (m, 2H), 7.70 (d, 1H), 7.55 (q, 1H), 7.49 (s, 1H), 7.29 (t, 1H), 2.80-2.90 (m, 5 H), 1.38 (t, 3H). IC50=7 nM.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08258130B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-9f090a2113e948358c4d591b83881145
Source note	uspto-grants-2012_09