Acetamide → HCID 11773465, compound

HRID 1813972Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=2[O:23][CH3:24])[N:3]=1.[C:25]([NH2:28])(=[O:27])[CH3:26]>[Cu]>[Cl:22][C:20]1[CH:19]=[CH:18][C:17]([O:23][CH3:24])=[C:16]([C:4]2[N:3]=[C:2]([NH:28][C:25](=[O:27])[CH3:26])[CH:7]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=3)[CH:5]=2)[CH:21]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of [2-chloro-6-(5-chloro-2-methoxy-phenyl)-pyridin-4-yl]-p-tolyl-amine (60 mg, 0.167 mmol) prepared according to Example 1, copper powder (100 mg, 1.54 mmol) and acetamide (2.0 g, 33.9 mmol) was heated at 180° C. for 3 hours. The mixture was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:1 followed by 3:2) to provide title compound (15 mg, 23% yield). 1H NMR (acetone-d6) δ 2.19 (s, 3H, CH3), 2.32 (s, 3H, CH3), 3.91 (s, 3H, CH3), 7.12 (d, 1H, J=8.8 Hz, Ar), 7.19-7.25 (m, 4H, Ar), 7.35 (dd, 1H, J=8.8 Hz, J=2.8 Hz, Ar), 7.47-7.48 (m, 1H, Ar), 7.86 (s, 1H, NH), 7.89 (d, 1H, J=2.8 Hz, Ar), 8.05 (s, 1H, NH).

Workup

customprepared
customThe mixture was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:1 followed by 3:2)

Sources & evidence

ORD record: ord-4ceaea598a46439481ef99de0c6e6407
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875781B2

Reaction notes

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