HCID 49839131, compound → 2-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-ol

HRID 1890022Notes

Reaction equation

HRID 1890022 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[N:33]=[C:18]4[C:19]([O:23]CC5C=CC=CC=5C#N)=[CH:20][CH:21]=[CH:22][N:17]4[N:16]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1>[Pd].CO>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[N:33]=[C:18]4[C:19]([OH:23])=[CH:20][CH:21]=[CH:22][N:17]4[N:16]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 49839131HCID 49839131, compound

Product 1

HCID 596124592-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-ol was prepared from combining 2-{2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yloxymethyl}-benzonitrile (30.0 mg, 0.68 mmol) and 10% palladium on carbon (50% Wet)(5:45:50, palladium:carbon black:water, 30 mg, 0.14 mmol) in methanol (10.0 mL) and shaking under an atmosphere of Hydrogen (45 psi) for 3 hours. Product was isolated as a mustard colored solid (14.0 mg, 63%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 10.45 (bs, 1H), 9.12 (s, 1H), 8.21 (dd, J=6.4 Hz, 1.0 Hz, 1H), 7.53 (d, J=8.8 Hz, 2H), 6.88 (d, J=8.8 Hz, 2H), 6.80-6.76 (m, 2H), 3.04-3.02 (m, 4H), 2.47-2.44 (m, 4H), 2.22 (s, 3H). MS=325.2 (MH)+.

Sources & evidence

ORD record
ord-1ed22322d7924dcb8f2790b7ccf634e8
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

Loading…