6-chloro-N-(4-methoxyphenyl)nicotinamide → HCID 21914603, compound

HRID 2108975Notes

Reaction equation

HRID 2108975 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.[CH:19]1([CH2:22][NH:23][C:24](=[O:41])[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[C:27](B3OC(C)(C)C(C)(C)O3)[CH:26]=2)[CH2:21][CH2:20]1>>[CH:19]1([CH2:22][NH:23][C:24]([C:25]2[CH:26]=[CH:27][C:28]([CH3:31])=[C:29]([C:2]3[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]4[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=4)=[O:7])=[CH:4][N:3]=3)[CH:30]=2)=[O:41])[CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 14832696-chloro-N-(4-methoxyphenyl)nicotinamide2×HCID 21914588N-cyclopropylmethyl-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide2×

Product 1

HCID 21914603HCID 21914603, compound

Procedure

6-[5-Cyclopropylmethylcarbamoyl-2-methyl-phenyl]-N-(4-methoxyphenyl)-nicotinamide was prepared from 6-chloro-N-(4-methoxyphenyl)nicotinamide (Intermediate 2) and N-cyclopropylmethyl-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (Intermediate 10) using General Method B. LCMS: retention time 3.12 min, MH+416. NMR: δH [2H6]-DMSO 10.39, (1H, s), 9.21, (1H, d), 8.63, (1H, t), 8.41, (1H, dd), 7.96, (1H, s), 7.86, (1H, d), 7.79, (1H, d), 7.71, (2H, d), 7.44, (1H, d), 6.96, (2H, d), 3.76, (3H, s), 3.15, (2H, t), 2.41, (3H, s), 1.03, (1H, m), 0.43, (2H, m), 0.23, (2H, m).

Sources & evidence

ORD record
ord-a1544a609eda4cc995f1812f82144099
Source dataset
uspto-grants-2009_04
Patent number
US07514456B2

Reaction notes

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