3-(4-Methylpiperazin-1-yl)aniline → HCID 59612547, compound

HRID 1890107Notes

Reaction equation

HRID 1890107 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][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)=[CH:21][CH:22]=[CH:23][N:18]2[N:17]=1>>[CH3:33][O:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][NH:24][C:20]2[C:19]3[N:18]([N:17]=[C:16]([NH:11][C:10]4[CH:12]=[CH:13][CH:14]=[C:8]([N:5]5[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]5)[CH:9]=4)[N:34]=3)[CH:23]=[CH:22][CH:21]=2)=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 115646133-(4-Methylpiperazin-1-yl)anilineHCID 67481371HCID 67481371, compound

Product 1

HCID 59612547HCID 59612547, compound

Procedure

N(8)-(4-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)-(4-methoxy-benzyl)-amine (99.9 mg, 0.346 mmol) in a manner analogous to Example 2d. Product isolated as a red foam (9.16 mg, 6%). 1H NMR (400 MHz, CD3OD, δ, ppm): 7.85 (d, J=5.9 Hz, 1H), 7.33 (m, 3H), 7.19-7.08 (m, 2H), 6.90 (d, J=8.0 Hz, 2H), 6.76 (t, J=14.4, 7.5 Hz, 1H), 6.57 (d, J=8.2 Hz, 1H), 6.44 (d, J=7.4 Hz, 1H), 4.42 (s, 2H), 3.78 (s, 3H), 3.23 (s, 4H), 2.64 (s, 4H), 2.37 (s, 3H). MS=444 (MH)+.

Sources & evidence

ORD record
ord-bd46f6e7d2ec4b24bf8e1c43dd23b6a8
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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