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

HRID 1246036Notes

Reaction equation

HRID 1246036 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-ff0b1b840e2542efa1ab74a50479ff81
Source dataset
uspto-grants-2006_10
Patent number
US07125898B2

Reaction notes

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