Diisopropylethylamine → HCID 10095012, compound

HRID 1742109Notes

Reaction equation

HRID 1742109 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]#[N:25])=[CH:14][CH:13]=2)[C:7](=[S:10])[NH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].C(N(CC)C(C)C)(C)C.[CH:35]1([CH2:41]Br)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>COCCO>[CH2:1]([C:5]1[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]#[N:25])=[CH:14][CH:13]=2)[C:7]([S:10][CH2:41][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)=[N:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 137636Cyclohexane, (bromomethyl)-HCID 10066359HCID 10066359, compound

Product 1

HCID 10095012HCID 10095012, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 147 mg (0.42 mmole) of 5-n-butyl-4-[(2'-cyanobiphenyl-4-yl)methyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione (from Example 15, Step C), 146 μl (108 mg, 0.84 mmole) of N,N-diisopropylethylamine, 117 μl (148 mg, 0.84 mmole) of cyclohexylmethyl bromide, and 1.5 ml of 2-methoxyethanol was stirred under N2 at 70° C. overnight and then at reflux for an additional 4 hours. The solution was concentrated in vacuo, and the residue was partitioned between 25 ml of ethyl acetate and 25 ml of 0.2 N HCl. The ethyl acetate layer was washed with saturated NACl, then dried over anhydrous MgSO4, filtered, and rotary evaporated in vacuo. Column chromatography of the residue on silica gel (elution with a gradient of 0-0.8% methanol in CH2Cl2) afforded 111 mg (59%) title compound as an oil, homogeneous by TLC in 19:1 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 445 (M+1)+.

Workup

  1. temperatureat reflux for an additional 4 hours
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue was partitioned between 25 ml of ethyl acetate and 25 ml of 0.2 N HCl
  4. washThe ethyl acetate layer was washed with saturated NACl
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customrotary evaporated in vacuo
  8. washColumn chromatography of the residue on silica gel (elution with a gradient of 0-0.8% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-b302998eda1c4d4083e0171edaf2c6ea
Source dataset
uspto-grants-1994_08
Patent number
US05336778

Reaction notes

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