4-Carboxy-1,2,3-triazole → HCID 178459157, compound

Participants

Role	Name	HCID	Charge
Reactant	4-Carboxy-1,2,3-triazole	HCID 140120	—
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 68181273	HCID 68181273	—
Catalyst	Diisopropylethylamine	HCID 81531	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 178459157	HCID 178459157	20,177.1%

Reaction Steps

1,2,3-Triazole-4-carboxylic acid (14 mg, 124 nmol), DIPEA (86.3 mL, 496 nmol) and HATU (47.1 mg, 124 nmol) were combined in DMF (0.2 mL) and stirred for 5 minutes at room temperature. This was then combined with (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid 2-(2-oxo-pyrrolidin-1-yl)-ethyl ester (52.6 mg, 124 nmol). The resulting mixture was stirred for 15 minutes and the reaction was quenched with AcOH. The product purified by preparative HPLC and lyophilized to yield the title compound (13 mg; purity 95%). MS m/z [M+H]+ calc'd for C28H33N5O5, 520.25. found 520.4.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08853427B2
Source dataset	uspto-grants-2014_10
ORD ID	ord-e8c61aa6b68c4831a579f50177445ca7
Source note	uspto-grants-2014_10