Toluene → N-[3-(4-{2-[4-(Cyclohexylmethyl)-1-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]ethyl}piperazino)phenyl]acetamide

HRID 1514173Notes

Reaction equation

HRID 1514173 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[N:17]([CH2:23][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[C:18](=[O:22])[N:19]([CH3:21])[N:20]=3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[C:30](OC(=O)C)(=[O:32])[CH3:31].C1(C)C=CC=CC=1>N1C=CC=CC=1>[CH:24]1([CH2:23][N:17]2[C:18](=[O:22])[N:19]([CH3:21])[N:20]=[C:16]2[CH2:15][CH2:14][N:11]2[CH2:10][CH2:9][N:8]([C:4]3[CH:3]=[C:2]([NH:1][C:30](=[O:32])[CH3:31])[CH:7]=[CH:6][CH:5]=3)[CH2:13][CH2:12]2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 7918Acetic AnhydrideHCID 595364685-{2-[4-(3-aminophenyl)piperazino]ethyl}-4-(cyclohexyl methyl)-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 25184737N-[3-(4-{2-[4-(Cyclohexylmethyl)-1-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]ethyl}piperazino)phenyl]acetamideYield 27%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-{2-[4-(3-aminophenyl)piperazino]ethyl}-4-(cyclohexylmethyl)-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (D16; 450 mg, 1.129 mmol) in dry pyridine (5 mL), acetic anhydride (0.112 mL, 1.185 mmol) was added at room temperature. The reaction mixture was stirred for 1 h, toluene (30 mL) was added and the solvents were removed in vacuo to afford a light-brown solid. Purification by preparative LC-MS afforded 133 mg (27%) of the title compound as a light brown powder.

Workup

  1. customthe solvents were removed in vacuo
  2. customto afford a light-brown solid
  3. customPurification by preparative LC-MS

Sources & evidence

ORD record
ord-06c7a31814f649cd90a215cb8432dfbf
Source dataset
uspto-grants-2012_07
Patent number
US08222254B2

Reaction notes

Loading…