Water → HCID 9802703, compound

HRID 967867Notes

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-0d695948b16143b199ead87b358308fe
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06956037B2

Reaction notes

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