Diisopropylethylamine → 2-(4,5-Dichloro-imidazol-1-yl)-N-[5-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-pyridin-3-yl]-acetamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	(4,5-Dichloro-1H-imidazol-1-yl)acetic acid	HCID 606695	—
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	(5-aminopyridin-3-yl)(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone	HCID 70817456	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(4,5-Dichloro-imidazol-1-yl)-N-[5-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-pyridin-3-yl]-acetamide	HCID 70817660	46%

Reaction Conditions

Temperature	50 °C

Reaction Steps

(4,5-Dichloro-imidazol-1-yl)-acetic acid (25.2 mg, 0.130 mmol) was added to (5-amino-pyridin-3-yl)-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone (28.1 mg, 0.1 mmol), HATU (49.4 mg, 0.130 mmol) and DIPEA (51.7 uL, 0.300 mmol) in anhydrous DMF (1 mL). The mixture was stirred at 50° C. for 16 hours and then evaporated in vacuo and purified by prep-HPLC (method 5) to afford the title compound in 46% yield, 21.2 mg.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08846698B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-8017ca28cd7a4aeea100dcd8dc1cc27c
Source note	uspto-grants-2014_09