Sodium Bicarbonate → 4-(4-(2-(5-Chloro-2-methyl-1H-indol-1-yl)propanoyl)-2-oxopiperazin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide

Participants

Role	Name	HCID	Charge
Reactant	Sodium Bicarbonate	HCID 516892	—
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	4-(2-Oxopiperazin-1-yl)-n-(thiazol-2-yl)benzenesulfonamide	HCID 59465631	—
Reactant	2-(5-Chloro-2-methyl-1h-indol-1-yl)propanoic acid	HCID 59465893	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-(4-(2-(5-Chloro-2-methyl-1H-indol-1-yl)propanoyl)-2-oxopiperazin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide	HCID 53627618	100%

Reaction Steps

Synthesized according to general procedure 14, method B. The reaction was set up with 4-(2-oxopiperazin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide (50 mg, 0.15 mmol), 2-(5-chloro-2-methyl-1H-indol-1-yl)propanoic acid (24 mg, 0.10 mmol), HATU reagent (76 mg, 0.20 mmol), sodium bicarbonate (17 mg, 0.20 mmol), and DMF (0.20 mL) to obtain the desired amide as a white solid (50 mg, 0.10 mmol, 32% yield). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA), m/z: M+1 obs=558.0; tR=3.02 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08163720B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-e92113aa14f745e5af1a8b1fd3ca450f
Source note	uspto-grants-2012_04