Dimethylformamide → HCID 67829298, compound

HRID 2379081Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([NH:9][CH2:10][CH2:11][N:12]2[C:17](=[O:18])[CH:16]=[CH:15][C:14]([C:19]([OH:21])=O)=[CH:13]2)=[O:8])[CH:2]=1.[CH3:22][N:23](C)C=O.C(N(CC)CC)C>C(OCC)(=O)C>[CH3:22][NH:23][C:19]([C:14]1[CH:15]=[CH:16][C:17](=[O:18])[N:12]([CH2:11][CH2:10][NH:9][C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[O:8])[CH:13]=1)=[O:21]

Participants

Conditions

Temperature: -8 °C

Procedure

To a 100 ml round bottomed flask fitted with a magnetic stirrer bar and nitrogen inlet was added 1,6-dihydro-l-[2-(3-pyridinylcarbonylamino)ethyl]-6-oxo-3-pyridinecarboxylic acid (0.22 g, 0.77 mmol) methylamine hydrochloride (0.104 g, 1.54 mmol), and dimethylformamide (25.5 ml). The reaction mixture was cooled in a -8° C. ice bath and treated with triethylamine (1.07 ml, 7.7 mmol) and propylphosphonic acid anhydride (0.55 ml, added as a 0.55 ml ethyl acetate solution, Angew. Chemie 1980, 92(2), 129). The flask was allowed to warm slowly to room temperature and stirred for 2.25 hours. The mixture was concentrated, slurried in aqueous sodium bicarbonate, and again concentrated. The residue was slurried in methanol and filtered. Further purification of the solid recovered from filtration via flash column chromotography (silica gel, 15-20% methanol/dichloromethane) gave the product, MP: 208°-210° C.

Workup

customTo a 100 ml round bottomed flask fitted with a magnetic stirrer bar and nitrogen inlet
temperatureto warm slowly to room temperature
concentrationThe mixture was concentrated
concentrationagain concentrated
filtrationfiltered
customFurther purification of the solid
filtrationrecovered from filtration via flash column chromotography (silica gel, 15-20% methanol/dichloromethane)
customgave the product, MP: 208°-210° C.

Sources & evidence

ORD record: ord-66747add9542482793d1e61c5fa94740
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05360808

Reaction notes

Loading…