Diisopropylethylamine → HCID 70896520, compound

https://huagongshe.com/reaction/1619290

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	N-Methyl-tert-butylamine	HCID 84552	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Reactant	HCID 70896531	HCID 70896531	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 70896520	HCID 70896520	65.2%

Reaction Conditions

Temperature	25 °C

Reaction Steps

To a solution of 5-bromo-3-cyano-pyridine-2-carboxylic acid (100 mg, 0.44 mmol) in dichloromethane (5 ml) at 0° C. were added DIPEA (0.226 ml, 1.32 mmol, 3 equiv.), methyl tert-butyl amine (0.079 ml, 0.661 mmol, 1.5 equiv.) and HBTU (250 mg, 0.661 mmol, 1.5 equiv.). The reaction mixture was stirred at 25° C. for 14 hours. The solvent was removed in vacuum and the resulting crude material was purified by column chromatography over normal silica gel (10-20% EtOAc in hexane) to afford 5-bromo-3-cyano-pyridine-2-carboxylic acid tert-butyl-methyl-amide (85 mg, 65%) as colorless oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08772300B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-ce7f018c4a6f44259cf83bcc62787a34
Source note	uspto-grants-2014_07