Diisopropylethylamine → (S)-2-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl 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	(S)-3-Boc-thiazolidine-2-carboxylic acid	HCID 14775612	—
Reactant	4-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide	HCID 59228792	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(S)-2-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl ester	HCID 57849787	—

Reaction Steps

(S)-Thiazolidine-2,3-dicarboxylic acid 3-tert-butyl ester (49.4 mg, 0.21 mmol) was dissolved in DMF (2 mL). DIEA (74 μL, 0.42 mmol) was added followed by HATU (80.7 mg, 0.21 mmol). The reaction was stirred at ambient temperature for 15 minutes. Then 4-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide (54.6 mg, 0.21 mmol) was added. The reaction was stirred at ambient temperature overnight and then heated to 50° C. for 7 hours. The reaction was cooled, filtered, and purified by reverse phase HPLC to give the desired product. Yield 30.5 mg. MS: 475.1 (M+H+); H1 NMR (DMSO-d6): δ(ppm) 0.54-0.75 (m, 4H), 1.22-1.47 (m, 9H), 2.79-2.90 (m, 1H), 3.05-3.25 (m, 2H), 3.55-3.75 (m, 1H), 5.33-5.50 (m, 2H), 7.78-7.98 (m, 5H), 8.40-8.48 (d, 1H), 12.50-12.59 (s, 1H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07595398B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-177bd830eebe4d178d796954300526e4
Source note	uspto-grants-2009_09