6-chloro-N-[2-(4-methylpiperazin-1-ylmethyl)phenyl]nicotinamide → 6-(5-Cyclopropylcarbamoyl-2-methyl-phenyl)-N-[2-(4-methylpiperazin-1-ylmethyl)phenyl]-nicotinamide

HRID 2108989Notes

Reaction equation

HRID 2108989 reaction equation
Cl[C:2]1[CH:24]=[CH:23][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][N:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)=[O:7])=[CH:4][N:3]=1.[CH:25]1([NH:28][C:29](=[O:46])[C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[C:32](B3OC(C)(C)C(C)(C)O3)[CH:31]=2)[CH2:27][CH2:26]1>>[CH:25]1([NH:28][C:29]([C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[C:32]([C:2]3[CH:24]=[CH:23][C:5]([C:6]([NH:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[CH2:15][N:16]4[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]4)=[O:7])=[CH:4][N:3]=3)[CH:31]=2)=[O:46])[CH2:26][CH2:27]1

Participants

3

Reactant 2

HCID 219145746-chloro-N-[2-(4-methylpiperazin-1-ylmethyl)phenyl]nicotinamide2×HCID 21914577N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide2×

Product 1

HCID 219146056-(5-Cyclopropylcarbamoyl-2-methyl-phenyl)-N-[2-(4-methylpiperazin-1-ylmethyl)phenyl]-nicotinamide

Procedure

6-(5-Cyclopropylcarbamoyl-2-methyl-phenyl)-N-[2-(4-methylpiperazin-1-ylmethyl)phenyl]-nicotinamide was prepared from 6-chloro-N-[2-(4-methylpiperazin-1-ylmethyl)phenyl]nicotinamide (Intermediate 5) 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 2.36 min, MH+484. NMR: δH [2H6]-DMSO 11.70, (1H, b), 9.23, (1H, s), 8.50, (1H, d), 8.38, (1H, d), 8.33, (1H, d), 7.92, (1H, s), 7.83, (2H, m), 7.43, (1H, d), 7.36, (1H, t), 7.29, (1H, d), 7.11, (1H, t), 3.77, (2H, s), 2.87, (1H, m), 2.67-2.24, (11H, m), 2.13, (3H, s), 0.70, (2H, m), 0.58, (2H, m).

Sources & evidence

ORD record
ord-ec3623cc0fe74a93b21b43b33da6850b
Source dataset
uspto-grants-2009_04
Patent number
US07514456B2

Reaction notes

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