Pyridine → HCID 10093668, compound

HRID 854784Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][C:18]2=[O:22])[C:13](O)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].C(Cl)(=O)C(Cl)=O.[NH2:29][C:30]1[CH:35]=[N:34][CH:33]=[CH:32][N:31]=1.N1C=CC=CC=1>C(Cl)Cl.CN(C)C=O.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][C:18]2=[O:22])[C:13]([NH:29][C:30]2[CH:35]=[N:34][CH:33]=[CH:32][N:31]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-(2-oxo-cyclopentyl)-propionic acid (125 mg, 0.36 mmol) in methylene chloride (3.62 mL) cooled to 0° C. was treated with a 2.0M solution of oxalyl chloride in methylene chloride (0.20 mL, 0.39 mmol) and a few drops of N,N-dimethylformamide. The reaction mixture was stirred at 0° C. for 10 min and at 25° C. for 20 min. The reaction mixture was then treated with a solution of 2-aminopyrazine (76 mg, 0.80 mmol) and pyridine (0.06 mL, 0.80 mmol) in tetrahydrofuran (1.81 mL). This solution was stirred at 25° C. for 1 h. At this time, the reaction was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 75/25 ethyl acetate/hexanes) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-(2-oxo-cyclopentyl)-N-pyrazin-2-yl-propionamide (77.6 mg, 50.7%) as a white foam: EI-HRMS m/e calcd for C19H20ClN3O4S (M+) 421.0863. found 421.0868.

Workup

stirringThis solution was stirred at 25° C. for 1 h
concentrationAt this time, the reaction was concentrated in vacuo

Sources & evidence

ORD record: ord-c774d2d3735a4502abd21c2e8af05feb
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259166B2

Reaction notes

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