1-(3-Bromophenyl)-4-methylpiperazine → [5-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-2-yl]-[3-(4-methyl-piperazin-1-yl)-phenyl]-amine

HRID 1889838Notes

Reaction equation

HRID 1889838 reaction equation
CS(C1C=CC(C2N=C(N)C=NC=2)=CC=1)(=O)=O.[CH3:18][S:19]([C:22]1[CH:27]=[CH:26][C:25]([C:28]2[N:33]3[N:34]=[C:35]([NH2:37])[N:36]=[C:32]3[CH:31]=[N:30][CH:29]=2)=[CH:24][CH:23]=1)(=[O:21])=[O:20].Br[C:39]1[CH:40]=[C:41]([N:45]2[CH2:50][CH2:49][N:48]([CH3:51])[CH2:47][CH2:46]2)[CH:42]=[CH:43][CH:44]=1>>[CH3:18][S:19]([C:22]1[CH:23]=[CH:24][C:25]([C:28]2[N:33]3[N:34]=[C:35]([NH2:37])[N:36]=[C:32]3[CH:31]=[N:30][CH:29]=2)=[CH:26][CH:27]=1)(=[O:20])=[O:21].[CH3:18][S:19]([C:22]1[CH:23]=[CH:24][C:25]([C:28]2[N:33]3[N:34]=[C:35]([NH:37][C:39]4[CH:44]=[CH:43][CH:42]=[C:41]([N:45]5[CH2:50][CH2:49][N:48]([CH3:51])[CH2:47][CH2:46]5)[CH:40]=4)[N:36]=[C:32]3[CH:31]=[N:30][CH:29]=2)=[CH:26][CH:27]=1)(=[O:20])=[O:21]

Participants

5

Reactant 3

HCID 534153291-(3-Bromophenyl)-4-methylpiperazineHCID 674787616-(4-Methylsulfonylphenyl)pyrazin-2-amineHCID 674788385-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine

Product 2

HCID 59612438[5-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-2-yl]-[3-(4-methyl-piperazin-1-yl)-phenyl]-amineHCID 674788385-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine

Procedure

6-(4-Methanesulfonyl-phenyl)-pyrazin-2-ylamine was prepared from 6-chloro-pyrazin-2-ylamine and (4-methylsulfonylphenyl)boronic acid in a manner analogous to Step 2c to afford an off-white solid (99%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.39 (s, 1H), 8.25 (d, 7.6 Hz, 2H) 8.02 (d, 7.6 Hz, 2H), 7.95 (s, 1H), 6.70 (bs, 2H), 3.26 (s, 3H). 107b) 5-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine was prepared from 6-(4-methanesulfonyl-phenyl)-pyrazin-2-ylamine in a manner analogous to Steps 2a-b. (37%), MS=291.1 (MH)+. 107c) [5-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-2-yl]-[3-(4-methyl-piperazin-1-yl)-phenyl]-amine was prepared from 5-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine and 1-(3-bromo-phenyl)-4-methyl-piperazine in a manner analogous to Step 2d and was isolated as a pale orange lyophilate (3% yield). 1H NMR (400 MHz, CDCl3, δ, ppm): 10.0 (s, 1H), 9.62 (bs, 1H), 9.14 (s, 1H), 8.42-8.40 (m, 3H), 8.20 (d, J=8.2 Hz, 2H), 7.58 (s, 1H), 7.18 (m, 1H), 7.05 (d, J=8.4 Hz, 1H), 6.60 (d, J=8.4 Hz, 1H), 3.72 (bd, 2H), 3.52 (bd, 2H), 3.39 (s, 3H), 3.17 (m, 2H), 2.93 (m, 2H), 2.87 (s, 3H). MS=464.1 (MH)+.

Workup

  1. customwas isolated as a pale orange lyophilate (3% yield)

Sources & evidence

ORD record
ord-5e3773ef551544b581b2c69de3ac83f6
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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