Methyl iodide → 4-(cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 1514171Notes

Reaction equation

HRID 1514171 reaction equation
[CH:1]1([CH2:7][N:8]2[C:12]([CH2:13][CH:14]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])[CH2:18][CH2:17]3)[CH3:15])=[N:11][NH:10][C:9]2=[O:30])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:31]CN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.CI>CC#N>[CH:1]1([CH2:7][N:8]2[C:12]([CH2:13][CH:14]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])[CH2:18][CH2:17]3)[CH3:15])=[N:11][N:10]([CH3:31])[C:9]2=[O:30])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 251847324-(cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 251847334-(cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 48%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a slurry of 4-(cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-2,4-dihydro-3H-1,2,4-triazol-3-one D14 (50 mg, 0.121 mmol) and PS-BEMP (83 mg, 0.1820 mmol, 2.2 mmol/g) in MeCN (2 mL), MeI (11.5 μL, 0.182 mmol) was added and the mixture was shaken at room temperature for 64 h. The resin was filtered and the filtrate was evaporated under reduced pressure. The resulting yellow oil was purified by flash chromatography (Biotage Isolute SI, 1 g column, gradient DCM to 1% MeOH in DCM) and afforded 25 mg (48%) 4-(cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one E37 as a white solid.

Workup

  1. filtrationThe resin was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe resulting yellow oil was purified by flash chromatography (Biotage Isolute SI, 1 g column, gradient DCM to 1% MeOH in DCM)

Sources & evidence

ORD record
ord-fec5b25457d349b9804e4550c4c3a6e4
Source dataset
uspto-grants-2012_07
Patent number
US08222254B2

Reaction notes

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