Triethylamine → HCID 15307996, compound

HRID 1289009Notes

Reaction equation

HRID 1289009 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12]3[O:19][N:20]=[CH:21][C:11]=3[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[CH3:24][C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27](Cl)=[O:28].C(N(CC)CC)C>O1CCCC1.O1CCOCC1.O1CCOCC1>[O:19]1[C:12]2[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:8]([C:6]([C:5]3[CH:22]=[CH:23][C:2]([NH:1][C:27](=[O:28])[C:26]4[CH:30]=[CH:31][CH:32]=[CH:33][C:25]=4[CH3:24])=[CH:3][CH:4]=3)=[O:7])[CH2:9][CH2:10][C:11]=2[CH:21]=[N:20]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 702762-Methylbenzoyl chlorideHCID 53877891HCID 53877891, compound

Product 1

HCID 15307996HCID 15307996, compound

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 22018518Dioxane tetrahydrofuranSolvent

Procedure

A partial solution of 0.250 g of 5,6-dihydro-6-(4-aminobenzoyl)-4H-isoxazolo[4,5-d][1]benzazepine in 4 ml of tetrahydrofuran-dioxane (1:3) under argon is treated with 160 μl of 2-methylbenzoyl chloride in 1.5 ml of dioxane followed by 114 μl of triethylamine and stirring continued for 4.5 hours at room temperature. The volatiles are evaporated in vacuo to a residue which is dissolved in methylene chloride containing methanol, washed with 10% NaHCO3 and brine, then treated with activated carbon. The mixture is filtered through MgSO4 and the filtrate filtered through silica gel with 15% ethylacetate in methylene chloride. The filtrate is evaporated in vacuo to a residue which is dissolved in methylene chloride, filtered through glass wool, evaporated to a residue which is dissolved in ethyl acetate by warming to give 0.25 g of the desired product as tan crystals, m.p. 257°-260° C. HR FABMS: (M+H)=424.1657.

Workup

  1. customThe volatiles are evaporated in vacuo to a residue which
  2. dissolutionis dissolved in methylene chloride
  3. additioncontaining methanol
  4. washwashed with 10% NaHCO3 and brine
  5. additiontreated with activated carbon
  6. filtrationThe mixture is filtered through MgSO4
  7. filtrationthe filtrate filtered through silica gel with 15% ethylacetate in methylene chloride
  8. customThe filtrate is evaporated in vacuo to a residue which
  9. dissolutionis dissolved in methylene chloride
  10. filtrationfiltered through glass wool
  11. customevaporated to a residue which
  12. dissolutionis dissolved in ethyl acetate
  13. temperatureby warming

Sources & evidence

ORD record
ord-7d74451553704b5b9d7af73a445ab3af
Source dataset
uspto-grants-1998_05
Patent number
US05747487

Reaction notes

Loading…