HCID 54220218, compound → HCID 24985097, compound

HRID 1887284Notes

Reaction equation

HRID 1887284 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](=[O:15])[NH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([NH:23][C:24]([C:26]1[S:30][C:29](Br)=[N:28][C:27]=1[CH3:32])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:16]([NH:23][C:24]([C:26]1[S:30][C:29]([N:13]2[CH:14]=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:10]=[CH:11][C:12]2=[O:15])=[N:28][C:27]=1[CH3:32])=[O:25])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 54220218HCID 54220218, compoundHCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide

Product 1

HCID 24985097HCID 24985097, compoundYield 32%

Procedure

Following the procedure as described in Example 3, making variations only as required to use 5-(benzyloxy)pyridin-2(1H)-one in place of 4-aminopyridin-2(1H)-one to react with N-benzyl-2-bromo-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 32% yield: mp 166-167° C.; 1H NMR (300 MHz, CDCl3) δ 8.36 (d, J=2.7 Hz, 1H), 7.48-7.22 (m, 11H), 6.61 (d, J=9.9 Hz, 1H), 6.45 (t, J=5.4 Hz, 1H), 4.98 (s, 2H), 4.56 (d, J=5.4 Hz, 2H), 2.70 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.2, 158.7, 153.3, 152.1, 143.3, 137.8, 136.1, 135.5, 128.7, 128.6, 127.9, 127.8, 127.6, 121.7, 112.0, 71.3, 44.0, 17.3; MS (ES+) m/z 432.2 (M+1).

Sources & evidence

ORD record
ord-82b0cc205f6a4b10b2e62acdd77d0e1e
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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