3-(4-Methylpiperazin-1-yl)aniline → N-Methyl-N-(3-{2-[3-(4-methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yl}-benzyl)-methanesulfonamide

HRID 472462Notes

Reaction equation

HRID 472462 reaction equation
Cl[C:2]1[N:23]=[C:5]2[C:6]([C:10]3[CH:11]=[C:12]([CH:20]=[CH:21][CH:22]=3)[CH2:13][N:14]([CH3:19])[S:15]([CH3:18])(=[O:17])=[O:16])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:24][N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=2)[NH2:34])[CH2:27][CH2:26]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:19][N:14]([CH2:13][C:12]1[CH:20]=[CH:21][CH:22]=[C:10]([C:6]2[C:5]3[N:4]([N:3]=[C:2]([NH:34][C:33]4[CH:35]=[CH:36][CH:37]=[C:31]([N:28]5[CH2:27][CH2:26][N:25]([CH3:24])[CH2:30][CH2:29]5)[CH:32]=4)[N:23]=3)[CH:9]=[CH:8][CH:7]=2)[CH:11]=1)[S:15]([CH3:18])(=[O:17])=[O:16]

Participants

4

Reactant 3

HCID 115646133-(4-Methylpiperazin-1-yl)anilineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 67479008N-[3-(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-benzyl]-N-methyl-methanesulfonamide

Product 1

HCID 59612356N-Methyl-N-(3-{2-[3-(4-methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yl}-benzyl)-methanesulfonamide

Procedure

N-Methyl-N-(3-{2-[3-(4-methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yl}-benzyl)-methanesulfonamide was prepared from N-[3-(2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-benzyl]-N-methyl-methanesulfonamide (75.0 mg, 0.214 mmol) and 3-(4-methylpiperazin-1-yl)aniline (45.0 mg, 0.235 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (24.0 mg, 0.0439 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a yellow foam (0.053 g, 49%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.43 (d, J=6.6 Hz, 1H), 8.05 (d, J=7.7 Hz, 1H), 7.93 (s, 1H), 7.60 (d, J=7.4 Hz, 1H), 7.52 (t, J=7.7 Hz, 1H), 7.42 (d, J=7.9 Hz, 1H), 7.32 (s, 1H), 7.22 (t, J=8.0 Hz, 1H), 7.01 (d, J=8.0 Hz, 1H), 6.97 (t, J=7.2 Hz, 1H), 6.84 (s, 1H), 6.58 (dd, J=8.2, 1.5 Hz, 1H), 4.42 (s, 2H), 3.29-3.25 (m, 4H), 2.88 (s, 3H), 2.83 (s, 3H), 2.62-2.57 (m, 4H), 2.37 (s, 3H). MS=506 (MH)+.

Sources & evidence

ORD record
ord-3d61da15aecf48a7b32f2d93700cf1a1
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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