4-Benzyloxy-2(1H)-pyridone → HCID 24983972, compound

HRID 1887304Notes

Reaction equation

HRID 1887304 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:18][C:19]([C:23]([NH:25][CH2:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[O:24])=[C:20]([CH3:22])[N:21]=1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:17]2[S:18][C:19]([C:23]([NH:25][CH2:26][C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[O:24])=[C:20]([CH3:22])[N:21]=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 666315502-Bromo-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

Product 1

HCID 24983972HCID 24983972, compoundYield 47%

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 2-bromo-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide in place of N-benzyl-2-bromo-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 47% yield: mp 208-209° C.; 1H-NMR (300 MHz, DMSO-d6) δ 8.86 (br s, 1H), 8.68-8.60 (m, 1H), 7.81-7.72 (m, 1H), 7.51-7.33 (m, 7H), 6.35-6.48 (m, 1H), 6.27 (s, 1H), 5.19 (s, 2H), 4.47 (s, 2H), 2.58 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 167.0, 161.5, 161.1, 153.5, 150.1, 135.2, 131.6, 128.5, 128.3, 128.0, 122.9, 103.9, 97.0, 70.3, 17.0; MS (ES+) m/z: 433.3 (M+1).

Sources & evidence

ORD record
ord-a6616c3ca4eb42989343b89313a05ba1
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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