1-(4-Bromophenyl)-4-methylpiperazine → [4-(4-Methyl-piperazin-1-yl)-phenyl]-{8-[4-(propane-2-sulfonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amine

HRID 472310Notes

Reaction equation

HRID 472310 reaction equation
[CH3:1][CH:2]([S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:14]3[N:15]([N:19]=[C:20]([NH2:22])[N:21]=3)[CH:16]=[CH:17][CH:18]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:3].Br[C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]2)=[CH:26][CH:25]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:36][N:33]1[CH2:34][CH2:35][N:30]([C:27]2[CH:26]=[CH:25][C:24]([NH:22][C:20]3[N:21]=[C:14]4[C:13]([C:10]5[CH:11]=[CH:12][C:7]([S:4]([CH:2]([CH3:1])[CH3:3])(=[O:6])=[O:5])=[CH:8][CH:9]=5)=[CH:18][CH:17]=[CH:16][N:15]4[N:19]=3)=[CH:29][CH:28]=2)[CH2:31][CH2:32]1

Participants

4

Reactant 3

HCID 118176751-(4-Bromophenyl)-4-methylpiperazineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 674813998-[4-(Propane-2-sulfonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Product 1

HCID 67478979[4-(4-Methyl-piperazin-1-yl)-phenyl]-{8-[4-(propane-2-sulfonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amine

Procedure

[4-(4-Methyl-piperazin-1-yl)-phenyl]-{8-[4-(propane-2-sulfonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amine was prepared from 8-[4-(propane-2-sulfonyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (75.0 mg, 0.237 mmol) and 1-(4-bromo-phenyl)-4-methyl-piperazine (75.0 mg, 0.294 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (48.0 mg, 0.0877 mmol) as the ligand in a manner analogous to Step 2d. The title compound was isolated as a yellow foam (0.051 g, 44%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.46 (d, J=6.7 Hz, 1H), 8.25 (d, J=7.8 Hz, 2H), 8.02 (d, J=7.8 Hz, 2H), 7.65 (d, J=7.3 Hz, 1H), 7.49 (d, J=7.8 HZ, 2H), 7.01-6.95 (m, 3H), 6.69 (s, 1H), 3.30-3.15 (m, 5H), 2.63-2.58 (m, 4H), 2.36 (s, 3H), 1.36 (d, J=6.7 Hz, 6H). MS=491 (MH)+.

Sources & evidence

ORD record
ord-40cae84f12d942d2bcee5062d5d1ff49
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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