3-Aminophenyl dimethylcarbamate → 3-(4-amino-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate

https://huagongshe.com/reaction/2098383

Participants

Role	Name	HCID	Charge
Reactant	3-Aminophenyl dimethylcarbamate	HCID 29877	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1-(tert-Butoxycarbonyl)-4-((tert-butoxycarbonyl)amino)piperidine-4-carboxylic acid	HCID 1268225	—
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	Tert-butyl 4-(tert-butoxycarbonylamino)-4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)piperidine-1-carboxylate	HCID 68992221	—
Solvent	Isopropyl Acetate	HCID 7915	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	3-(4-amino-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate	HCID 57920209	45%

Reaction Steps

Preparation of tert-butyl 4-(tert-butoxycarbonylamino)-4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)piperidine-1-carboxylate. N-Boc-amino-(4-N-Boc-piperidinyl) carboxylic acid (0.114 g, 0.33 mmol), HATU (0.151 g, 0.40 mmol) and N,N-diisopropylethylamine (128 mg, 1.0 mmol) were combined in isopropyl acetate (2.3 mL) and stirred at room temperature for 15 minutes. 3-aminophenyl dimethylcarbamate (0.072 g, 0.40 mmol) was added, and the mixture heated at 80° C. for 1.5 hours. The reaction mixture was allowed to cool, diluted with EtOAc, washed with 2 N Na2CO3, 1 N HCl, and brine, and then dried over MgSO4 and concentrated. Purification by silica gel chromatography (60% EtOAc/hexanes) gave the title compound (0.075 g, 45%) as a white solid. MS (ES+) [M+NH4]+=524.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08450332B2
Source dataset	uspto-grants-2013_05
ORD ID	ord-be79bfa656cc463fbc13b9df02fd7ad7
Source note	uspto-grants-2013_05