4-(4-Methylpiperazin-1-yl)aniline → N(2)-[4-(4-Methyl-piperazin-1-yl)-phenyl]-N(8)-pyridin-3-ylmethyl-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine

HRID 1889898Notes

Reaction equation

HRID 1889898 reaction equation
Cl[C:2]1[N:18]=[C:5]2[C:6]([NH:10][CH2:11][C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=2)[CH2:22][CH2:21]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:19][N:20]1[CH2:21][CH2:22][N:23]([C:26]2[CH:31]=[CH:30][C:29]([NH:32][C:2]3[N:18]=[C:5]4[C:6]([NH:10][CH2:11][C:12]5[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=5)=[CH:7][CH:8]=[CH:9][N:4]4[N:3]=3)=[CH:28][CH:27]=2)[CH2:24][CH2:25]1

Participants

4

Reactant 3

HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 67481455(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-pyridin-3-ylmethyl-amine

Product 1

HCID 49839376N(2)-[4-(4-Methyl-piperazin-1-yl)-phenyl]-N(8)-pyridin-3-ylmethyl-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine

Procedure

N(2)-[4-(4-Methyl-piperazin-1-yl)-phenyl]-N(8)-pyridin-3-ylmethyl-[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)-pyridin-3-ylmethyl-amine (75.0 mg, 0.289 mmol) and 4-(4-methyl-piperazin-1-yl)-phenylamine (61.0 mg, 0.319 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 (0.075 g, 63%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.66 (s, 1H), 8.55 (d, J=4.1 Hz, 1H), 7.83 (d, J=6.5 Hz, 1H), 7.72 (d, J=7.8 Hz, 1H), 7.47 (d, J=8.9 Hz, 2H), 7.31-7.25 (m, 1H), 6.95 (d, J=8.9 Hz, 2H), 6.66 (t, J=7.3 Hz, 1H), 6.57 (s, 1H), 6.30 (d, J=7.7 Hz, 1H), 5.08 (t, J=5.6 Hz, 1H), 4.50 (d, J=5.8 Hz, 2H), 3.17-3.13 (m, 4H), 2.62-2.57 (m, 4H), 2.36 (s, 3H). MS=415 (MH)+.

Sources & evidence

ORD record
ord-afa157fa76bf4770affb8c3e5fd56c91
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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