Hydrochloric Acid → HCID 86674663, compound

HRID 245769Notes

Reaction equation

Cl.[Cl:2][C:3]1[C:4]([CH2:9][NH2:10])=[N:5][CH:6]=[CH:7][N:8]=1.[CH3:11][N:12]1[C:16](=[O:17])[CH2:15][CH:14]([C:18](O)=[O:19])[CH2:13]1.C(N(CC)C(C)C)(C)C.C(N=C=NCCCN(C)C)C.Cl.ON1C2N=CC=CC=2N=N1>ClCCl.ClCCl.CO>[Cl:2][C:3]1[C:4]([CH2:9][NH:10][C:18]([CH:14]2[CH2:15][C:16](=[O:17])[N:12]([CH3:11])[CH2:13]2)=[O:19])=[N:5][CH:6]=[CH:7][N:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(3-Chloropyrazin-2-yl)methanamine hydrochloride (content 77%, 1.634 g, 6.99 mmol) and 1-methyl-5-oxopyrrolidine-3-carboxylic acid (1.000 g, 6.99 mmol) were suspended in dichloromethane (20 ml) and the reaction mixture was cooled to 0° C. under an argon atmosphere. N,N-diisopropylethylamine (3.05 ml, 17.48 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide) hydrochloride (1.474 g, 7.69 mmol) and 1-hydroxy-7-azabenzotriazole (0.476 g, 3.50 mmol) were added and the reaction mixture was stirred at room temperature overnight. Reaction was worked up by evaporting the solvents and a dark brown oil was obtained. This crude product was submitted to column chromatography (silica gel; dichloromethane/methanol 96/4) to yield impure material that was further purified by column chromatography (silica gel; dichloromethane/methanol 99/1) to give N-((3-chloropyrazin-2-yl)methyl)-1-methyl-5-oxopyrrolidine-3-carboxamide (1.24 g).

Workup

customReaction
customa dark brown oil was obtained
customto yield impure material that
customwas further purified by column chromatography (silica gel; dichloromethane/methanol 99/1)

Sources & evidence

ORD record: ord-b0b4c23b18c64a508e9fa6a46383eac0
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658794B2

Reaction notes

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