Triethylamine → HCID 178437647, compound

HRID 1241500Notes

Reaction equation

HRID 1241500 reaction equation
[NH2:1][CH:2]([C:5]1[C:6](=[O:17])[NH:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:9][N:10]=1)[CH2:3][CH3:4].C(N(CC)CC)C.[C:25]([C@@H:29]1[CH2:34][CH2:33][C@H:32]([C:35](Cl)=O)[CH2:31][CH2:30]1)([CH3:28])([CH3:27])[CH3:26].O=P(Cl)(Cl)Cl.[OH-].[Na+]>ClC(Cl)C.ClCCl.O>[C:25]([C@@H:29]1[CH2:30][CH2:31][C@H:32]([C:35]2[N:10]3[C:5]([C:6](=[O:17])[NH:7][C:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[N:9]3)=[C:2]([CH2:3][CH3:4])[N:1]=2)[CH2:33][CH2:34]1)([CH3:28])([CH3:26])[CH3:27]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 1355940666-(1-Aminopropyl)-3-phenyl-1,2,4-triazin-5(4H)-oneHCID 178445652HCID 178445652, compound

Product 1

HCID 178437647HCID 178437647, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

20.45 g (0.09 mol) 6-(1-Aminopropyl)-3-phenyl-1,2,4-triazin-5(4H)-one (Example 34A) are dissolved in dichloroethane, 502 g (5.08 mol) triethylamine and 19.8 g (0.10 mol) cis-4-tert-butylcyclohexanecarbonyl chloride are added. The solution is stirred at reflux for three hours, then 20.42 g (0.13 mol) phosphoroxychloride are added. The solution is stirred at reflux for another 4 hours and, after cooling down to room temperature, water, sodium hydroxide and then dichloromethane are added. The organic phase is evaporated to dryness in vacuo, and the residue triturated with diethylether and filtrated. The solid is dissolved in methanol (75%)/dichloromethane (25%), the dichloromethane is evaporated in vacuo, and the crystallized product is filtered and dried.

Workup

  1. temperatureat reflux for three hours
  2. stirringThe solution is stirred
  3. temperatureat reflux for another 4 hours
  4. customThe organic phase is evaporated to dryness in vacuo
  5. customthe residue triturated with diethylether
  6. filtrationfiltrated
  7. dissolutionThe solid is dissolved in methanol (75%)/dichloromethane (25%)
  8. customthe dichloromethane is evaporated in vacuo
  9. filtrationthe crystallized product is filtered
  10. customdried

Sources & evidence

ORD record
ord-49c55a6b0fc84b11ad493ffd0960498b
Source dataset
uspto-grants-2006_10
Patent number
US07115602B2

Reaction notes

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