Diisopropylethylamine → 3-(1-{6-[2-(3,5-Difluoro-phenyl)-5,5-dimethyl-piperidine-1-carbonyl]-pyrimidin-4-yl}-piperidin-4-yl)-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

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	6-[4-(7-Methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]pyrimidine-4-carboxylic acid	HCID 58386616	—
Reactant	(S)-2-(3,5-difluorophenyl)-5,5-dimethylpiperidine	HCID 66722231	—
Solvent	Dimethylformamide	HCID 6228	—
Product	3-(1-{6-[2-(3,5-Difluoro-phenyl)-5,5-dimethyl-piperidine-1-carbonyl]-pyrimidin-4-yl}-piperidin-4-yl)-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one	HCID 67339620	—

Reaction Steps

65 mg (0.16 mmol) 6-[4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid and 70 mg (0.16 mmol) (S)-2-(3,5-difluorophenyl)-5,5-dimethylpiperidine in 0.04 mL (0.72 mmol) DIPEA and 0.80 mL DMF were combined with 65 mg (0.17 mmol) HATU and stirred overnight at RT. Then the reaction mixture was purified by preparative HPLC-MS. The product-containing fractions were combined and freeze-dried.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08829006B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-22415976832d45038f4bc43fe77f46a8
Source note	uspto-grants-2014_09