Phenethyl tosylate → N-Benzyl-3-methyl-5-(2-oxo-4-phenethoxypyridin-1(2H)-yl)thiophene-2-carboxamide

HRID 1887316Notes

Reaction equation

CC1C=CC(S([O:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=O)=O)=CC=1.[CH2:20]([NH:27][C:28]([C:30]1[S:31][C:32]([N:36]2[CH:41]=[CH:40][C:39](O)=[CH:38][C:37]2=[O:43])=[CH:33][C:34]=1[CH3:35])=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:20]([NH:27][C:28]([C:30]1[S:31][C:32]([N:36]2[CH:41]=[CH:40][C:39]([O:11][CH2:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:38][C:37]2=[O:43])=[CH:33][C:34]=1[CH3:35])=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Reactant 2

HCID 20522Phenethyl tosylate

HCID 54742340N-benzyl-5-(4-hydroxy-2-oxopyridin-1(2H)-yl)-3-methylthiophene-2-carboxamide

Product 1

HCID 24983970N-Benzyl-3-methyl-5-(2-oxo-4-phenethoxypyridin-1(2H)-yl)thiophene-2-carboxamideYield 59%

Procedure

Following the procedure as described in Example 9, making variations only as required to use phenethyl 4-methylbenzenesulfonate in place of 2-cyclopropylethyl 4-methylbenzenesulfonate to react with N-benzyl-5-(4-hydroxy-2-oxopyridin-1(2H)-yl)-3-methylthiophene-2-carboxamide, the title compound was obtained as a colorless solid in 59% yield: mp 159-160° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.55 (t, J=5.9 Hz, 1H), 8.12 (d, J=7.9 Hz, 1H), 7.35-7.20 (m, 11H), 6.18 (dd, J=7.9, 2.6 Hz, 1H), 6.06 (d, J=2.6 Hz, 1H), 4.41 (d, J=6.0 Hz, 2H), 4.27 (t, J=6.7 Hz, 2H), 3.04 (t, J=6.6 Hz, 2H), 2.42 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 166.3, 162.4, 161.0, 139.6, 138.8, 137.7, 137.1, 135.0, 128.8, 128.3, 128.2, 127.3, 127.1, 126.6, 126.3, 120.5, 102.4, 96.8, 68.8, 42.5, 34.2, 15.5; MS (ES+) m/z 445.3 (M+1).

Sources & evidence

ORD record: ord-039cff81c64a4bb191b4685b577699cf
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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