Triethylamine → HCID 67027472, compound

To a solution of 2-chlorothiazole-5-carboxylic acid (815 mg, 5 mmol) in dichloromethane (10 mL) was slowly added oxalyl chloride (0.53 mL, 6 mmol) and then N,N dimethylformamide (1 drop) with stirring. The mixture was stirred for 16 hours, following which the organics were removed in vacuo, and the residues azeotroped with toluene (100 ml). The crude material was dissolved in dichloromethane (10 mL) and slowly added to a stirred suspension of azetidine hydrochloride (560 mg, 6 mmol) and triethylamine (2.5 mL, 18 mmol) in dichloromethane (25 mL). The mixture was stirred at ambient temperature for 2 hours before the organics were removed in vacuo. The residue was dissolved in ethyl acetate (50 mL) and water (25 mL), the organic layer washed with brine (25 mL), dried (MgSO4) and evaporated to a residue which was chromatographed on silica with 40% ethyl acetate in iso-hexane as eluant to give 5-(azetidin-1-ylcarbonyl)-2-chloro-1,3-thiazoline. 1H NMR δ (CDCl3): 2.4 (m, 2H), 4.1-4.4 (m, 4H), 4.55 (m, 1H), 7.2 (s, 1H) and 7.75 (s, 1H); m/z 203 (M+H)+.

1. customorganics were removed in vacuo
2. customthe residues azeotroped with toluene (100 ml)
3. dissolutionThe crude material was dissolved in dichloromethane (10 mL)
4. stirringThe mixture was stirred at ambient temperature for 2 hours before the
5. customorganics were removed in vacuo
6. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
7. washwater (25 mL), the organic layer washed with brine (25 mL)
8. dry with materialdried (MgSO4)
9. customevaporated to a residue which
10. customwas chromatographed on silica with 40% ethyl acetate in iso-hexane as eluant

ORD record

ord-b4cc4a38448944f19f37af470427ffa8

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977328B2