4-(4-Methylpiperazin-1-yl)aniline → HCID 49839130, compound

HRID 472490Notes

Reaction equation

HRID 472490 reaction equation
Cl[C:2]1[N:24]=[C:5]2[C:6]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=2)[CH2:28][CH2:27]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:23][N:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][O:10][C:6]1[C:5]2[N:4]([N:3]=[C:2]([NH:38][C:35]3[CH:34]=[CH:33][C:32]([N:29]4[CH2:28][CH2:27][N:26]([CH3:25])[CH2:31][CH2:30]4)=[CH:37][CH:36]=3)[N:24]=2)[CH:9]=[CH:8][CH:7]=1)[S:19]([CH3:22])(=[O:21])=[O:20]

Participants

4

Reactant 3

HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 67479220HCID 67479220, compound

Product 1

HCID 49839130HCID 49839130, compound

Procedure

N-Methyl-N-(2-{2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yloxymethyl}-phenyl)-methanesulfonamide was prepared from N-[2-(2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yloxymethyl)-phenyl]-N-methyl-methanesulfonamide (102.0 mg, 0.2781 mmol) and 4-(4-methyl-piperazin-1-yl)-phenylamine (60.0 mg, 0.314 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (30.0 mg, 0.0549 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a brown foam (0.016 g, 11%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.07 (d, J=6.7 Hz, 1H), 7.74-7.69 (m, 1H), 7.46 (d, J=8.1 Hz, 2H), 7.43-7.38 (m, 2H), 7.34-7.30 (m, 1H), 6.96 (d, J=8.1 Hz, 2H), 6.90 (d, J=7.8 Hz, 1H), 6.73 (t, J=7.3 Hz, 1H), 6.62 (s, 1H), 5.49 (br s, 2H), 3.32 (s, 3H), 3.18-3.13 (m, 4H), 2.99 (s, 3H), 2.62-2.57 (m, 4H), 2.36 (s, 3H). MS=522 (MH)+.

Sources & evidence

ORD record
ord-6a398ec357994d45bfed04517a64e30a
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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