3-(4-Methylpiperazin-1-yl)aniline → N(8)-(3-Methoxy-benzyl)-N(2)-[3-(4-methyl-piperazin-1-yl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine

HRID 472649Notes

Reaction equation

HRID 472649 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=2)[NH2:11])[CH2:4][CH2:3]1.Cl[C:16]1[N:34]=[C:19]2[C:20]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=3)=[CH:21][CH:22]=[CH:23][N:18]2[N:17]=1>>[CH3:33][O:32][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=1)[CH2:25][NH:24][C:20]1[C:19]2[N:18]([N:17]=[C:16]([NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[C:8]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]4)[CH:9]=3)[N:34]=2)[CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 115646133-(4-Methylpiperazin-1-yl)anilineHCID 67481427(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(3-methoxy-benzyl)-amine

Product 1

HCID 59612435N(8)-(3-Methoxy-benzyl)-N(2)-[3-(4-methyl-piperazin-1-yl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine

Procedure

N(8)-(3-Methoxy-benzyl)-N(2)-[3-(4-methyl-piperazin-1-yl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine was prepared from 3-(4-methylpiperazin-1-yl)aniline (74.2 mg, 0.388 mmol) and (2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(3-methoxy-benzyl)-amine (99.9 mg, 0.346 mmol) in a manner analogous to Example 2d. Product isolated as a red foam (11.16 mg, 7%). 1H NMR (400 MHz, CD3OD, δ, ppm): 7.85 (d, J=7.0 Hz, 1H), 7.32 (s, 1H), 7.24 (t, J=15.5, 7.8 Hz, 1H), 7.19-7.09 (m, 2H), 6.99 (s, 2H), 6.82 (d, J=8.0 Hz, 1H), 6.75 (t, J=14.2, 7.0 Hz, 1H), 6.57 (d, J=7.8 Hz, 1H), 6.41 (d, J=7.5 Hz, 1H), 4.48 (m, 2H), 3.77 (s, 3H), 3.24 (s, 4H), 2.65 (s, 4H), 2.37 (s, 3H). MS=444 (MH)+.

Sources & evidence

ORD record
ord-de3664f13de344b0bd7d1f705ff255a1
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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