4-Benzyloxy-2(1H)-pyridone → HCID 57744481, compound

HRID 1887303Notes

Reaction equation

HRID 1887303 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:17]1[S:21][C:20]([C:22]([NH:24][CH2:25][CH3:26])=[O:23])=[C:19]([CH3:27])[CH:18]=1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:17]2[S:21][C:20]([C:22]([NH:24][CH2:25][CH3:26])=[O:23])=[C:19]([CH3:27])[CH:18]=2)[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 68617641HCID 68617641, compound

Product 1

HCID 57744481HCID 57744481, compoundYield 45%

Procedure

Following the procedure as described in Example 3, making variations only as required to use 4-(benzyloxy)pyridin-2(1H)-one in place of 4-aminopyridin-2(1H)-one to react with 5-bromo-N-ethyl-3-methylthiophene-2-carboxamide in place of N-benzyl-2-bromo-4-methylthiazole-5-carboxamide, the title compound was obtained as a light yellow solid in 45% yield: mp 158-160° C.; 1H NMR (300 MHz, CDCl3) δ 7.54 (d, J=7.8 Hz, 1H), 7.43-7.36 (m, 5H), 6.82 (s, 1H), 6.13 (dd, J=7.8, 2.7 Hz, 1H), 6.06 (d, J=2.7 Hz, 1H), 5.84 (br s, 1H), 5.04 (s, 2H), 3.49-3.38 (m, 2H), 2.51 (s, 3H), 1.22 (t, J=7.3 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 166.8, 162.9, 162.3, 139.4, 139.0, 134.8, 134.7, 128.8, 128.6, 127.7, 127.5, 122.2, 103.2, 98.2, 70.6, 34.8, 15.8, 14.9; MS (ES+) m/z 369.3 (M+1).

Sources & evidence

ORD record
ord-6ac935056d9244a388356addc16f5089
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

Loading…