Hydrogen Sulfide → HCID 54034171, compound

HRID 1432914Notes

Reaction equation

HRID 1432914 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=2)[C:13](=[O:26])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S.CI.[N:30]1C=CC=CC=1>CCN(CC)CC>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24](=[NH:30])[NH2:25])=[CH:22][CH:23]=2)[C:13](=[O:26])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 402Hydrogen SulfideHCID 1049PyridineHCID 6328Methyl iodideHCID 53741197HCID 53741197, compound

Product 1

HCID 54034171HCID 54034171, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 4-(4-cyanobenzyl)-3-oxopiperazine-1-carboxylic acid benzyl ester (2.4 g, 6.87 mmol) in 30 mL of pyridine and 3 ml of Et3N is saturated with H2S. The resulting mixture is sealed and stirred for 16 hours. After this time, the solution is concentrated. The residue is dissolved in 30 mL of acetone and methyl iodide (19.4 g, 137 mmol) is added. The solution is refluxed for 2 hours. After this time, the solution is concentrated. The residue is dissolved in MeOH (40 mL) and NH4OAc (5.0 g, 65 mol) is added. The solution is reluxed for 3 hours. After this time, the solution is concentrated. The crude product is purified by RP-HPLC eluting in a gradient of CH3CN to 60% CH3CN/H2O(0.1%TFA). The appropriate collected fractions are lyophilized to give the product as a white foam. MS (FAB) m/z 367, (M+H).

Workup

  1. customThe resulting mixture is sealed
  2. concentrationAfter this time, the solution is concentrated
  3. dissolutionThe residue is dissolved in 30 mL of acetone
  4. temperatureThe solution is refluxed for 2 hours
  5. concentrationAfter this time, the solution is concentrated
  6. dissolutionThe residue is dissolved in MeOH (40 mL)
  7. waitThe solution is reluxed for 3 hours
  8. concentrationAfter this time, the solution is concentrated
  9. customThe crude product is purified by RP-HPLC
  10. washeluting in a gradient of CH3CN to 60% CH3CN/H2O(0.1%TFA)
  11. customThe appropriate collected fractions

Sources & evidence

ORD record
ord-102b0ba063b24b638e7156658acba26f
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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