Dimethylformamide → HCID 19369475, compound

HRID 1292153Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([OH:18])=[O:17].CCN=C=N[CH2:27][CH2:28][CH2:29][N:30](C)C.Cl.[CH3:34][N:35]([CH:37]=[O:38])C>CN(C)C1C=CN=CC=1>[C:29]([C:28]1[C:37](=[O:38])[NH:35][C:34]2[C:11]([CH:27]=1)=[C:2]([O:17][C:16](=[O:18])[C:15]1[CH:19]=[CH:20][CH:21]=[C:13]([O:12][CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)[CH:14]=1)[CH:3]=[CH:4][C:5]=2[CH3:6])#[N:30]

Participants

Conditions

Temperature: 50 °C

Procedure

A liquid mixture of 0.838 g (3 mmol) of 3-(2-quinolinylmethoxy)benzoic acid, 0.601 g (3 mmol) of 3-cyano-5-hydroxy-8-methylcarbostyryl, 50 ml of DMF, 0.931 g (6 mmol) of WSC.HCl and 0.73 g (0.6 mmol) of 4-dimethylaminopyridine was stirred under an argon gas stream at a bath temperature of 50° C. for 2 days. The solvent was distilled off from the reaction mixture under reduced pressure. Water was added to the residue, and the resulting mixture was extracted with a 2:1 mixed solvent of CHCl3 and MeOH. The extract was washed with water, dried over MgSO4 and then concentrated. The concentrate was allowed to stand overnight, whereby 0.495 g of the title compound was obtained as yellow powder (yield: 35.8%).

Workup

distillationThe solvent was distilled off from the reaction mixture under reduced pressure
additionWater was added to the residue
extractionthe resulting mixture was extracted with a 2:1 mixed solvent of CHCl3 and MeOH
washThe extract was washed with water
dry with materialdried over MgSO4
concentrationconcentrated
waitto stand overnight

Sources & evidence

ORD record: ord-eedfe1e95b05405eb54ad82ba6e97984
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05756518

Reaction notes

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