1-[(4-Bromophenyl)methyl]-4-methylpiperazine → [8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-amine

HRID 1889774Notes

Reaction equation

HRID 1889774 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3[N:13]([N:17]=[C:18]([NH2:20])[N:19]=3)[CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br[C:22]1[CH:35]=[CH:34][C:25]([CH2:26][N:27]2[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]2)=[CH:24][CH:23]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3[N:13]([N:17]=[C:18]([NH:20][C:22]4[CH:23]=[CH:24][C:25]([CH2:26][N:27]5[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]5)=[CH:34][CH:35]=4)[N:19]=3)[CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

4

Reactant 3

HCID 221976121-[(4-Bromophenyl)methyl]-4-methylpiperazineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 575023768-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Product 1

HCID 67481480[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-amine

Procedure

[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-amine was prepared from 8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (50.0 mg, 0.173 mmol) and 1-(4-bromo-benzyl)-4-methyl-piperazine (56.0 mg, 0.208 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (20.0 mg, 0.0366 mmol) as the ligand in a manner analogous to Step 2d and was isolated as a pale yellow foam (0.010 g, 12%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.50 (d, J=6.4 Hz, 1H), 8.24 (d, J=8.2 Hz, 2H), 8.09 (d, J=8.2 Hz, 2H), 7.66 (d, J=7.1 Hz, 1H), 7.54 (d. J=7.8 Hz, 2H), 7.31 (d, J=7.9 Hz, 2H), 7.02 (t, J=6.7 Hz, 1H), 6.86 (s, 1H), 3.49 (s, 2H), 3.11 (s, 3H), 2.46 (br s, 8H), 2.29 (s, 3H). MS=477 (MH)+.

Sources & evidence

ORD record
ord-e0122639b0ea410b9ef51130b16f1f56
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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