Diisopropylethylamine → 2-[((S)-1-Benzyloxycarbonyl-pyrrolidine-2-carbonyl)-amino]-4-(4-cyclopropylcarbamoyl-phenyl)-thiazole-5-carboxylic acid methyl ester

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Benzyloxycarbonyl-L-proline	HCID 101987	—
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-[5-(3-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester	HCID 57849886	—
Reactant	2-Amino-4-(4-cyclopropylcarbamoyl-phenyl)-thiazole-5-carboxylic acid methyl ester	HCID 86616445	—
Product	2-[((S)-1-Benzyloxycarbonyl-pyrrolidine-2-carbonyl)-amino]-4-(4-cyclopropylcarbamoyl-phenyl)-thiazole-5-carboxylic acid methyl ester	HCID 57849671	—

Reaction Steps

In a similar procedure as described for the synthesis of Compound 5312 (Example 312), 2-amino-4-(4-cyclopropylcarbamoyl-phenyl)-thiazole-5-carboxylic acid methyl ester (0.098 g, 0.31 mmol) was treated with HATU (0.18 g, 0.46 mmol), DIEA (0.3 mL, 2.3 mmol), and (S)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (0.12 g, 0.46 mmol) to furnish the desired product. 1HNMR (DMSO-d6) δ(ppm)12.90-12.88 (d, 1H), 8.89-8.85 (m, 1H), 8.51-8.50 (d, 1H), 7.86-7.72 (m, 4H), 7.37-7.33 (m, 2H), 7.15-7.09 (m, 2H), 5.09-4.87 (m, 2H), 4.51-4.49 (m, 1H), 3.74-3.72 (m, 3H), 3.53-3.47 (m, 1H), 2.88-2.84 (m, 1H), 2.45 (m, 1H), 1.91-1.87 (m, 3H), 0.71-0.59 (m, 4H); MS: 549.2 (M+H+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07595398B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-87149e005a804700b2cdf33eaa433719
Source note	uspto-grants-2009_09