Benzylamine → HCID 86753041, compound

HRID 482445Notes

Reaction equation

HRID 482445 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:26])[N:7]([CH3:25])[C:8]([C:12]3[CH:24]=[CH:23][C:15]([CH2:16][P:17](=[O:22])([O-])[O:18][CH2:19][CH3:20])=[CH:14][CH:13]=3)=[N:9]2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH2:31]([NH2:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C1CCN2C(=NCCC2)CC1>ClCCl.CN(C=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:26])[N:7]([CH3:25])[C:8]([C:12]3[CH:13]=[CH:14][C:15]([CH2:16][P:17]([NH:38][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)(=[O:22])[O:18][CH2:19][CH3:20])=[CH:23][CH:24]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 24386Thionyl ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86753042HCID 86753042, compound

Product 1

HCID 86753041HCID 86753041, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

The compound obtained in Example 61 (0.50 g), 1 ml of DMF and 0.15 g of thionyl chloride were suspended in 10 ml of dichloromethane and refluxed for 3 hours. After completion of the reaction, the reaction mixture was allowed to cool, 10 ml of dichloromethane containing 0.14 g of benzylamine and 0.58 g of DBU was added dropwise, and the mixture was stirred at room temperature for 18 hours. After the reaction, the organic layer was washed with diluted hydrochloric acid, distilled water and saturated brine in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (eluent: dichloromethane: methanol=30:1) and recrystallized from ethyl acetate-n-hexane to provide 0.28 g of the desired compound as colorless crystals. Table 3 shows the chemical structure and physical property (melting point) of the compound obtained.

Workup

  1. temperaturerefluxed for 3 hours
  2. customAfter completion of the reaction
  3. temperatureto cool
  4. customAfter the reaction
  5. washthe organic layer was washed with diluted hydrochloric acid
  6. distillationdistilled water and saturated brine in this order
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue thus obtained
  10. customwas purified by silica gel column chromatography (eluent: dichloromethane: methanol=30:1)
  11. customrecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-5722521188a448199f67ecf88197abee
Source dataset
uspto-grants-1998_08
Patent number
US05798344

Reaction notes

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