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

HRID 472340Notes

Reaction equation

HRID 472340 reaction equation
Cl[C:2]1[N:21]=[C:5]2[C:6]([NH:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[S:17]([CH3:20])(=[O:19])=[O:18])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([C:29]2[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=2)[CH2:25][CH2:24]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:20][S:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[NH:10][C:6]1[C:5]2[N:4]([N:3]=[C:2]([NH:35][C:32]3[CH:31]=[CH:30][C:29]([N:26]4[CH2:25][CH2:24][N:23]([CH3:22])[CH2:28][CH2:27]4)=[CH:34][CH:33]=3)[N:21]=2)[CH:9]=[CH:8][CH:7]=1)(=[O:19])=[O:18]

Participants

4

Reactant 3

HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 67478992(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(2-methanesulfonyl-phenyl)-amine

Product 1

HCID 67481457N(8)-(2-Methanesulfonyl-phenyl)-N(2)-[4-(4-methyl-piperazin-1-yl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine

Procedure

N(8)-(2-Methanesulfonyl-phenyl)-N(2)-[4-(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-phenyl)-amine (57.0 mg, 0.176 mmol) and 4-(4-methyl-piperazin-1-yl)-phenylamine (37.0 mg, 0.193 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 tan foam (0.037 g, 44%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.46 (s, 1H), 8.11 (d, J=6.1 Hz, 1H), 7.98 (d, J=7.7 Hz, 1H), 7.57-7.45 (m, 4H), 7.11 (t, J=7.3 Hz, 1H), 6.96 (d, J=7.7 Hz, 2H), 6.78 (t, J=7.0 Hz, 1H), 6.67 (s, 1H), 3.18-3.12 (m, 7H), 2.62-2.57 (m, 4H), 2.36 (s, 3H). MS=478 (MH)+.

Sources & evidence

ORD record
ord-e04335a3dfc443f1a294ba8d5efd34b9
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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