Diisopropylethylamine → (R)-4-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-thiazolidine-3-carboxylic acid benzyl ester

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	(R)-3-((Benzyloxy)carbonyl)thiazolidine-4-carboxylic acid	HCID 11119045	—
Reactant	4-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide	HCID 59228792	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(R)-4-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-thiazolidine-3-carboxylic acid benzyl ester	HCID 57849681	—

Reaction Steps

(R)-Thiazolidine-3,4-dicarboxylic acid 3-benzyl ester (52.5 mg, 0.20 mmol) was dissolved in DMF (2 mL). DIEA (68.5 μL, 0.39 mmol) was added followed by HATU (74.8 mg, 0.20 mmol). The reaction was stirred at ambient temperature for 15 minutes. Then 4-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide (51.1 mg, 0.20 mmol) was added, and the reaction was stirred at ambient temperature overnight. The reaction was filtered and purified by reverse phase HPLC to give the desired product. Yield 18.5 mg. MS: 509.1 (M+H+); H1 NMR (DMSO-d6): δ(ppm) 0.54-0.75 (m, 4H), 2.78-2.90 (m, 1H), 4.51-4.59 (m, 1H), 4.62-4.70 (m, 1H), 4.83-5.18 (m, 3H), 7.07-7.43 (m, 5H), 7.77-7.99 (m, 5H), 8.39-8.47 (m, 1H), 12.55-12.64 (s, 1H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07595398B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-fab90fcae1694212b57050207bde958f
Source note	uspto-grants-2009_09