Diisopropylethylamine → HCID 59140928, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-(3-Pyridinyl)-2-thiazolamine	HCID 154893	—
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	1-Cbz-pyrrolidine	HCID 10608307	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 59140928	HCID 59140928	—

Reaction Steps

Pyrrolidine-1-carboxylic acid benzyl ester, (224 mg, 0.9 mmol) was combined with 376 mg (1.0 mmol) of HATU. This mixture was dissolved in 15 ml of DMF. To this solution was added DIEA (1.8 mmol, 0.3 mL). This solution was stirred at room temperature for 1.5 hours. To this solution was then added 4-pyridin-3-yl-thiazol-2-ylamine (100 mg, 0.56 mg). Reaction mixture was stirred at room temperature overnight and then purified using reverse phase HPLC. MS: 409.1 (M+H+); H1 NMR (DMSO-d6): δ(ppm) (HCl salt) 12.62 (s, 1H), 9.28 (s, 1H), 8.78 (s, 1H), 8.03 (m, 2H), 7.38 (m, 3H), 7.04 (d, 2H), 5.00 (m, 2H), 4.53 (m, 1H), 3.62 (m, 2H), 2.22 (m, 1H), 1.89 (m, 4H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07595398B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-8d20a0ced70d470d87e668b52970f89b
Source note	uspto-grants-2009_09