Diisopropylethylamine → (3S,9aS)-tert-butyl 8-(2-(2-(1H-tetrazol-1-yl)pyrimidin-5-yl)acetyl)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate

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	(3S,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate	HCID 71271513	—
Reactant	[2-(1H-tetrazol-1-yl)pyrimidin-5-yl]acetic acid	HCID 89619099	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	(3S,9aS)-tert-butyl 8-(2-(2-(1H-tetrazol-1-yl)pyrimidin-5-yl)acetyl)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate	HCID 89619169	—

Reaction Steps

To a solution of (3S,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate (46 mg, 0.123 mmol) and 2-(2-(1H-tetrazol-1-yl)pyrimidin-5-yl)acetic acid (30.4 mg, 0.147 mmol) in DMF (2 mL) was added HATU (70.1 mg, 0.184 mmol) and diisopropylethylamine (64.4 μl, 0.369 mmol) and the resulting solution was stirred at rt for 1 h. Ethyl acetate (50 mL) was added and the organic phase was washed with brine (3×50 mL), dried over sodium sulphate, concentrated and the residue was purified on TLC using 10% methanol/methylene chloride to give title compound, LC/MS: [(M+23)]+=585.23; [(M+1-100-28)]+=435.20.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09206199B2
Source dataset	uspto-grants-2015_12
ORD ID	ord-16545ed74809423796f6c1dd04556f38
Source note	uspto-grants-2015_12