4-(4-Methylpiperazin-1-yl)aniline → HCID 59612558, compound

HRID 472497Notes

Reaction equation

HRID 472497 reaction equation
Cl[C:2]1[N:25]=[C:5]2[C:6]([NH:10][CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])[CH3:12])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:26][N:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=2)[CH2:29][CH2:28]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:24][N:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH:11]([NH:10][C:6]1[C:5]2[N:4]([N:3]=[C:2]([NH:39][C:36]3[CH:35]=[CH:34][C:33]([N:30]4[CH2:29][CH2:28][N:27]([CH3:26])[CH2:32][CH2:31]4)=[CH:38][CH:37]=3)[N:25]=2)[CH:9]=[CH:8][CH:7]=1)[CH3:12])[S:20]([CH3:23])(=[O:22])=[O:21]

Participants

4

Reactant 3

HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 67479350HCID 67479350, compound

Product 1

HCID 59612558HCID 59612558, compound

Procedure

197 h) N-Methyl-N-[2-(1-{2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino}-ethyl)-phenyl]-methanesulfonamide was prepared from N-{2-[1-(2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-ethyl]-phenyl}-N-methyl-methanesulfonamide (75.0 mg, 0.197 mmol) and 4-(4-methyl-piperazin-1-yl)-phenylamine (42.0 mg, 0.220 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (18.0 mg, 0.0329 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a pale yellow solid (0.008 g, 8%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.77-7.25 (m, 8H), 7.00-6.93 (m, 2H), 6.65-6.30 (m, 3H), 5.40-5.24 (m, 1H), 5.00-4.91 (m, 1H), 3.35-3.29 (m, 3H), 3.19-3.13 (m, 4H), 3.07-3.01 (m, 3H), 2.63-2.58 (m, 4H), 2.36 (s, 3H), 1.72-1.55 (m, 3H). MS=535 (MH)+.

Sources & evidence

ORD record
ord-a5d824cd521b4a099fc7a48be37e97f6
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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