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

HRID 2108990Notes

Reaction equation

HRID 2108990 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.[CH3:25][C:26]1[CH:39]=[CH:38][C:29]([C:30]([NH:32][N:33]2[NH:37][CH:36]=[CH:35][S:34]2)=[O:31])=[CH:28][C:27]=1B1OC(C)(C)C(C)(C)O1>>[CH3:22][N:19]1[CH2:20][CH2:21][N:16]([CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:6](=[O:7])[C:5]2[CH:23]=[CH:24][C:2]([C:27]3[CH:28]=[C:29]([C:30](=[O:31])[NH:32][N:33]4[NH:37][CH:36]=[CH:35][S:34]4)[CH:38]=[CH:39][C:26]=3[CH3:25])=[N:3][CH:4]=2)[CH2:17][CH2:18]1

Participants

3

Reactant 2

HCID 219145746-chloro-N-[2-(4-methylpiperazin-1-ylmethyl)phenyl]nicotinamide2×HCID 219146524-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-N-(thiadiazol-2-yl)-benzamide2×

Product 1

HCID 21914610N-[2-(4-Methylpiperazin-1-ylmethyl)phenyl]-6-[2-methyl-5-(thiadiazol-2-ylcarbamoyl)-phenyl]-nicotinamide

Procedure

N-[2-(4-Methylpiperazin-1-ylmethyl)phenyl]-6-[2-methyl-5-(thiadiazol-2-ylcarbamoyl)-phenyl]-nicotinamide was prepared from 6-chloro-N-[2-(4-methylpiperazin-1-ylmethyl)phenyl]nicotinamide (Intermediate 5) and 4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-N-(thiadiazol-2-yl)-benzamide (Intermediate 12) using General Method B. LCMS: retention time 2.43 min, MH+528. NMR: δH [2H6]-DMSO 13.07, (1H, b), 11.74, (1H, s), 9.26, (1H, s), 9.21, (1H, s), 8.43, (1H, d), 8.34, (1H, d), 8.29, (1H, s), 8.12, (1H, d), 7.93, (1H, d), 7.56, (1H, d), 7.36, (1H, t), 7.29, (1H, d), 7.11, (1H, t), 3.78, (2H, s), 2.67-2.26, (11H, m), 2.11, (3H, s).

Sources & evidence

ORD record
ord-147a96b8ad084883973003eabd97f306
Source dataset
uspto-grants-2009_04
Patent number
US07514456B2

Reaction notes

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