Water → HCID 9802703, compound

HRID 1369503Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4]Br.[C:6]([C:8]1[CH:33]=[CH:32][C:11]([C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([CH3:31])=[C:19]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[CH:20]=2)=[O:13])=[CH:10][CH:9]=1)#[N:7].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:6]([C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([CH3:31])=[C:19]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:4][CH2:3][O:2][CH3:1])=[CH:25][CH:24]=3)[CH:20]=2)=[O:13])=[CH:32][CH:33]=1)#[N:7]

Participants

Conditions

Temperature: 80 °C

Procedure

2-Bromoethyl methyl ether (0.023 ml) was added to a suspension of N-[5-(4-cyanobenzamido)-2-methylphenyl]-4-hydroxybenzamide (0.06 g) and potassium carbonate (0.045 g) in DMF (3 ml) and the reaction mixture was stirred and heated to 80° C. for 5 hours. The mixture was poured into water and extracted with ethyl acetate. The organic extract was dried (MgSO4) and evaporated. The residue was triturated under diethyl ether and the resultant solid was isolated and dried under vacuum at 55° C. There was thus obtained the title compound (0.038 g); NMR Spectrum: (DMSOd6) 2.19 (s, 3H), 3.27 (s, 3H), 3.66 (s, 2H), 4.17 (m, 2H), 7.04 (d, 2H), 7.24 (d, 1H), 7.57 (d, 1H), 7.82 (s, 1H), 7.96 (m, 4H), 8.1 (d, 2H), 9.71 (s, 1H), 10.44 (s, 1H); Mass Spectrum: M−H− 428.

Workup

extractionextracted with ethyl acetate
extractionThe organic extract
dry with materialwas dried (MgSO4)
customevaporated
customThe residue was triturated under diethyl ether
customthe resultant solid was isolated
customdried under vacuum at 55° C

Sources & evidence

ORD record: ord-64467690f13448978fedca2993f0b384
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06579872B1

Reaction notes

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