Iodoethane → 4-(Cyclohexylmethyl)-2-ethyl-5-{2-[4-(2-methoxyphenyl)piperazino]ethyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 1514175Notes

Reaction equation

HRID 1514175 reaction equation
[CH3:1][CH2:2]N(P1(N(C)CCCN1C)=NC(C)(C)C)CC.[CH:19]1([CH2:25][N:26]2[C:30]([CH2:31][CH2:32][N:33]3[CH2:38][CH2:37][N:36]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=4[O:45][CH3:46])[CH2:35][CH2:34]3)=[N:29][NH:28][C:27]2=[O:47])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C(I)C>CC#N>[CH:19]1([CH2:25][N:26]2[C:30]([CH2:31][CH2:32][N:33]3[CH2:34][CH2:35][N:36]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=4[O:45][CH3:46])[CH2:37][CH2:38]3)=[N:29][N:28]([CH2:1][CH3:2])[C:27]2=[O:47])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 251844534-(cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazino]ethyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 251847984-(Cyclohexylmethyl)-2-ethyl-5-{2-[4-(2-methoxyphenyl)piperazino]ethyl}-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 59.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a slurry of PS-BEMP (0.682 g, 1.50 mmol, 2.2 mmol/g) and 4-(cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazino]ethyl}-2,4-dihydro-3H-1,2,4-triazol-3-one (E17; 300 mg, 0.75 mmol) in MeCN (10 mL), ethyl iodide (0.12 mL, 1.50 mmol) was added and the reaction mixture was stirred at room temperature for 3 days. The resin was filtered, washed with MeOH (10 mL) and the solvent was evaporated in vacuo to afford 280 mg crude foamy solid. Purification by preparative LC-MS afforded 190 mg (59%) of the title compound as a glassy solid.

Workup

  1. filtrationThe resin was filtered
  2. washwashed with MeOH (10 mL)
  3. customthe solvent was evaporated in vacuo
  4. customto afford 280 mg crude foamy solid
  5. customPurification by preparative LC-MS

Sources & evidence

ORD record
ord-45ddbc530bbb4d63b77cc34ce98bf23f
Source dataset
uspto-grants-2012_07
Patent number
US08222254B2

Reaction notes

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