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

HRID 2037260Notes

Reaction equation

HRID 2037260 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([NH:22][C:23](=[O:40])[C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26](B3OC(C)(C)C(C)(C)O3)[CH:25]=2)[CH2:21][CH2:20]1>>[CH:19]1([NH:22][C:23]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([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:25]=2)=[O:40])[CH2:20][CH2:21]1

Participants

3

Reactant 2

HCID 14832696-chloro-N-(4-methoxyphenyl)nicotinamide2×HCID 21914577N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide2×

Product 1

HCID 219145916-[5-Cyclopropylcarbamoyl-2-methyl-phenyl]-N-(4-methoxyphenyl)nicotinamide

Procedure

6-[5-Cyclopropylcarbamoyl-2-methyl-phenyl]-N-(4-methoxyphenyl)-nicotinamide was prepared from 6-chloro-N-(4-methoxyphenyl)nicotinamide (Intermediate 2) and N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (Intermediate 8) using General Method B. LCMS: retention time 2.96 min, MH+ 402. NMR: δH [2H6]-DMSO 10.38, (1H, s), 9.20, (1H, s), 8.49, (1H, d), 8.40, (1H, dd), 7.91, (1H, s), 7.82, (1H, d), 7.76, (1H, d), 7.71, (2H, d), 7.43, (1H, d), 6.96, (2H, d), 3.76, (3H, s), 2.87, (1H, m), 2.40, (3H, s), 0.70, (2H, m), 0.58, (2H, m).

Sources & evidence

ORD record
ord-f92aa86b7b494b7db9891e200ed4aa9b
Source dataset
uspto-grants-2013_11
Patent number
US08575204B2

Reaction notes

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