Cyclopropylamine → (S)-2-[4-(5-Cyclopropylcarbamoyl-furan-2-yl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

Participants

Role	Name	HCID	Charge
Reactant	Cyclopropylamine	HCID 69828	—
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)-2-[4-(5-Carboxy-furan-2-yl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester	HCID 86616437	—
Product	(S)-2-[4-(5-Cyclopropylcarbamoyl-furan-2-yl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester	HCID 57849692	—

Reaction Steps

In a similar procedure as described for the synthesis of Compound 5352 (Example 352), treatment of (S)-2-[4-(5-Carboxy-furan-2-yl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester with HATU (0.23 g, 0.6 mmol), DIEA (0.2 mL, 1.53 mmol), and cyclopropylamine (0.1 1 mL) furnished the desired product. 1HNMR (DMSO-d6) δ(ppm) 12.59-12.57 (d, 1H), 8.42-8.39 (m, 1H), 7.64-7.62 (d, 1H), 7.36-7.30 (m, 2H), 7.14-7.10 (m, 3H), 6.73-6.70 (m, 1H), 5.10-4.87 (m, 2H), 4.51-4.43 (m, 2H), 3.52-3.36 (m, 2H), 2.80-2.77, (m, 2H), 2.27-2.24 (m, 1H), 1.94-1.83 (m, 3H), 0.73-0.58 (m, 4H); MS: 481.2 (M+H+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07595398B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-0e6025725e3f4c88ba59a3a706b0fb21
Source note	uspto-grants-2009_09