Diisopropylethylamine → 2-(4-{4-[5-(2-Oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-phenyl}-thiazol-2-ylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Biotin	HCID 171548	—
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	(S)-2-[4-(4-Amino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester	HCID 86616427	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(4-{4-[5-(2-Oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-phenyl}-thiazol-2-ylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester	HCID 76582788	—

Reaction Steps

70 mg (0.28 mmol) of biotin was dissolved in 5 mL of dry DMF. To this solution were added DIEA (0.34 mmol, 0.06 mL) and HATU (0.28 mmol, 0.1 g). This solution was stirred at room temperature for 2 hours. 80 mg (0.189 mmol) of Compound 5050 was then added to the reaction mixture and stirred at room temperature overnight. Reaction mixture was evaporated to dryness and redissolved in 5 mL of DMF and purified using reverse phase HPLC. MS: 649.2 (M+H+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07595398B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-ed3e280b401445f6909cf5d00d6e164e
Source note	uspto-grants-2009_09