3-(4-Methylpiperazin-1-yl)aniline → N(8)-(2-Methanesulfonyl-benzyl)-N(2)-[3-(4-methyl-piperazin-1-yl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine

HRID 472413Notes

Reaction equation

HRID 472413 reaction equation
Cl[C:2]1[N:22]=[C:5]2[C:6]([NH:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[S:18]([CH3:21])(=[O:20])=[O:19])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:31]=[C:32]([CH:34]=[CH:35][CH:36]=2)[NH2:33])[CH2:26][CH2:25]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:21][S:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][NH:10][C:6]1[C:5]2[N:4]([N:3]=[C:2]([NH:33][C:32]3[CH:34]=[CH:35][CH:36]=[C:30]([N:27]4[CH2:26][CH2:25][N:24]([CH3:23])[CH2:29][CH2:28]4)[CH:31]=3)[N:22]=2)[CH:9]=[CH:8][CH:7]=1)(=[O:20])=[O:19]

Participants

4

Reactant 3

HCID 115646133-(4-Methylpiperazin-1-yl)anilineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 67479011(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(2-methanesulfonyl-benzyl)-amine

Product 1

HCID 67481402N(8)-(2-Methanesulfonyl-benzyl)-N(2)-[3-(4-methyl-piperazin-1-yl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine

Procedure

N(8)-(2-Methanesulfonyl-benzyl)-N(2)-[3-(4-methyl-piperazin-1-yl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine was prepared from (2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(2-methanesulfonyl-benzyl)-amine (75.0 mg, 0.223 mmol) and 3-(4-methylpiperazin-1-yl)aniline (47.0 mg, 0.246 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (25.0 mg, 0.0457 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a tan foam (0.023 g, 21%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.11 (d, J=8.0 Hz, 1H), 7.85 (d, J=6.5 Hz, 1H), 7.66-7.59 (m, 2H), 7.54-7.49 (m, 1H), 7.27-7.23 (m, 1H), 7.21 (t, J=8.2 Hz, 1H), 7.02 (d, J=9.2 Hz, 1H), 6.72-6.67 (m, 2H), 6.57 (dd, J=8.2, 1.6 Hz, 1H), 6.43 (d, J=7.6 hZ, 1H), 5.33 (t, J=6.1 Hz, 1H), 4.96 (d, J=6.2 Hz, 2H), 3.29-3.24 (m, 4H), 3.16 (s, 3H), 2.61-2.56 (m, 4H), 2.36 (s, 3H). MS=492 (MH)+.

Sources & evidence

ORD record
ord-86c1e46598da462fa86aabf35d7115f9
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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