6-chloro-N-(3-methoxybenzyl)nicotinamide → N-(3-Methoxybenzyl)-6-[5-(thiophen-3-ylcarbonylamino)-2-methyl-phenyl]-nicotinamide

HRID 1246043Notes

Reaction equation

HRID 1246043 reaction equation
Cl[C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)=[O:7])=[CH:4][N:3]=1.[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([C:30]2[CH:34]=[CH:33][S:32][CH:31]=2)=[O:29])=[CH:23][C:22]=1B1OC(C)(C)C(C)(C)O1>>[CH3:17][O:16][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[CH2:9][NH:8][C:6](=[O:7])[C:5]1[CH:18]=[CH:19][C:2]([C:22]2[CH:23]=[C:24]([NH:27][C:28]([C:30]3[CH:34]=[CH:33][S:32][CH:31]=3)=[O:29])[CH:25]=[CH:26][C:21]=2[CH3:20])=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 94957946-chloro-N-(3-methoxybenzyl)nicotinamide2×HCID 21914662N-[4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-thiophenecarboxamide2×

Product 1

HCID 21914660N-(3-Methoxybenzyl)-6-[5-(thiophen-3-ylcarbonylamino)-2-methyl-phenyl]-nicotinamide

Procedure

N-(3-Methoxybenzyl)-6-[5-(thiophen-3-ylcarbonylamino)-2-methyl-phenyl]-nicotinamide was prepared from 6-chloro-N-(3-methoxybenzyl)nicotinamide (Intermediate 3) and N-[4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]thiophene-3-amide (Intermediate 14) using General Method B. LCMS: retention time 3.27 min, MH+ 458. NMR: δH [2H6]-DMSO 10.12,(1H, s), 9.29, (1H, t), 9.15,(1H, d), 8.35–8.32,(2H, m), 7.86,(1H, s), 7.78,(1H, d), 7.68–7.65, (3H, m), 7.32–7.24,(2H, m), 6.94,(2H, m), 6.84,(2H, d), 4.51,(2H, d), 3.75,(3H, s), 2.32, (3H, s).

Sources & evidence

ORD record
ord-4b67d4cfd7004268adec163d40eb92d7
Source dataset
uspto-grants-2006_10
Patent number
US07125898B2

Reaction notes

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