6-chloro-N-(4-methoxyphenyl)nicotinamide → N-(4-Methoxyphenyl)-6-[2-methyl-5-(thiazol-2-ylcarbamoyl)-phenyl]-nicotinamide

HRID 2037262Notes

Reaction equation

HRID 2037262 reaction equation
Cl[C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.[CH3:19][C:20]1[CH:33]=[CH:32][C:23]([C:24]([NH:26][C:27]2[S:28][CH:29]=[CH:30][N:31]=2)=[O:25])=[CH:22][C:21]=1B1OC(C)(C)C(C)(C)O1>>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6](=[O:7])[C:5]2[CH:17]=[CH:18][C:2]([C:21]3[CH:22]=[C:23]([C:24](=[O:25])[NH:26][C:27]4[S:28][CH:29]=[CH:30][N:31]=4)[CH:32]=[CH:33][C:20]=3[CH3:19])=[N:3][CH:4]=2)=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 14832696-chloro-N-(4-methoxyphenyl)nicotinamide2×HCID 219145174-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-N-(thiazol-2-yl)-benzamide2×

Product 1

HCID 21914585N-(4-Methoxyphenyl)-6-[2-methyl-5-(thiazol-2-ylcarbamoyl)-phenyl]-nicotinamide

Procedure

N-(4-Methoxyphenyl)-6-[2-methyl-5-(thiazol-2-ylcarbamoyl)-phenyl]-nicotinamide was prepared from 6-chloro-N-(4-methoxyphenyl)nicotinamide (Intermediate 2) and 4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-N-(thiazol-2-yl)-benzamide (Intermediate 11) using General Method B. LCMS: retention time 3.22 min, MH− 445. NMR: δH [2H6]-DMSO 12.72, (1H, s), 10.40, (1H, s), 9.22, (1H, d), 8.44, (1H, dd), 8.24, (1H, s), 8.09, (1H, d), 7.87, (1H, d), 7.71, (2H, d), 7.58, (1H, d), 7.53, (1H, d), 7.30, (1H, d), 6.97, (2H, d), 3.76, (3H, s), 2.48, (3H, s).

Sources & evidence

ORD record
ord-5596caa269ae4a31a21bd16c4ab7257a
Source dataset
uspto-grants-2013_11
Patent number
US08575204B2

Reaction notes

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