Cyclopentylamine → (R)-1-tert-butyl 3-methyl 4-((1-(cyclopentylamino)-4,4,4-trifluoro-1-oxobutan-2-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate

https://huagongshe.com/reaction/1968225

Participants

Role	Name	HCID	Charge
Reactant	Cyclopentylamine	HCID 2906	—
Reactant	4-Methylmorpholine	HCID 7972	—
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	HCID 58293478	HCID 58293478	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	(R)-1-tert-butyl 3-methyl 4-((1-(cyclopentylamino)-4,4,4-trifluoro-1-oxobutan-2-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate	HCID 58293445	—

Reaction Conditions

Temperature	43 °C

Reaction Steps

To (R)-2-((1-(tert-butoxycarbonyl)-3-(methoxycarbonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methylamino)-4,4,4-trifluorobutanoic acid was added THF (2 mL), HATU (94 mg, 0.246 mmol), cyclopentanamine (70.0 mg, 0.822 mmol) and 4-methylmorpholine (83 mg, 0.822 mmol). The resulting suspension was stirred at 43° C. for 36 h to afford the title compound, which was used in the next step without further purification. [M+H] calc'd for C24H31F3N4O5, 513; found, 513.6.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08420816B2
Source dataset	uspto-grants-2013_04
ORD ID	ord-4206276b4f61481f9047168737dc7d0d
Source note	uspto-grants-2013_04