Diisopropylethylamine → HCID 57513812, compound

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	4-(4-Fluorophenyl)-5-propyl-1,3-thiazol-2-amine	HCID 28065420	—
Reactant	HCID 57513846	HCID 57513846	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 57513812	HCID 57513812	—

Reaction Steps

A mixture of 70 mg of (S)-1-benzooxazol-2-yl-pyrrolidine-2-carboxylic acid (intermediate 2), 71 mg of 4-(4-fluoro-phenyl)-5-propyl-thiazol-2-ylamine (intermediate 1), 128 mg of HATU and 0.16 mL of DIEA in CH2Cl2 was stirred at room temperature overnight. Solvent was evaporated and crude material was purified by chromatography (C-18, CH3CN/H2O) to provide the title compound. 1H NMR (400 MHz, CHLOROFORM-d) ppm 0.98 (t, J=7.33 Hz, 3H) 1.62-1.81 (m, 2H) 2.03-2.37 (m, 4H) 2.52-2.68 (m, 1H) 2.82 (t, 2H) 3.76 (q, J=8.84 Hz, 1H) 3.92 (br. s., 1H) 4.88 (br. s., 1H) 7.02-7.14 (m, 3H) 7.22 (t, J=7.71 Hz, 1H) 7.32 (d, J=7.96 Hz, 1H) 7.41-7.58 (m, 3H). MS m/z 451.0 (M+H), 449.1 (M−H). HRMS calcd for C24H23FN4O2S=450.15257, found=450.15235. HPLC (0-95% ACN in 20 min using 0.1% TFA on 150 mm Atlantis C18 column) Rt=15.36.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08703761B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-fbcb44f57e404deb83319a1857df3d7c
Source note	uspto-grants-2014_04