Triethylamine → HCID 20232130, compound

HRID 2290265Notes

Reaction equation

HRID 2290265 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[NH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[C:16]([O:20][C:21]([NH:23][CH2:24][C:25](O)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C(N(CC)CC)C.ClC(OCC)=O>CN(C=O)C.C(Cl)Cl>[C:16]([O:20][C:21]([NH:23][CH2:24][C:25]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]([CH3:15])[NH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:6][CH:7]=1)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 133860336-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

Product 1

HCID 20232130HCID 20232130, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (2.28 g) in DMF (30 ml) was added dropwise a solution of mixed anhydride prepared from N-t-butoxycarbonylglycine (3.912 g), triethylamine (2.371 g) and ethyl chloroformate (2.425 g) in methylene chloride (15 ml) with stirring under ice-cooling. The stirring was continued for 1 hour at the same temperature. The mixture was filtered and the filtrate was evaporated in vacuo. The residue was dissolved in ethyl acetate, washed successively with water, an aqueous solution of sodium bicarbonate and water, dried and evaporated in vacuo. The residue was dissolved in methanol (12 ml) and conc. ammonia (1.5 ml) was added thereto. After stirring for 2 hours at room temperature, the resulting precipitates were collected by filtration, washed with methanol, and dried to give 6-[4-[N-(t-butoxycarbonyl)glycylamino]phenyl]-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (1.74 g).

Workup

  1. temperaturecooling
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed successively with water
  6. dry with materialan aqueous solution of sodium bicarbonate and water, dried
  7. customevaporated in vacuo
  8. dissolutionThe residue was dissolved in methanol (12 ml)
  9. additionconc. ammonia (1.5 ml) was added
  10. stirringAfter stirring for 2 hours at room temperature
  11. customthe resulting precipitates
  12. filtrationwere collected by filtration
  13. washwashed with methanol
  14. customdried

Sources & evidence

ORD record
ord-f77dcebea79544c6a687a4f1acaeeef4
Source dataset
uspto-grants-1986_10
Patent number
US04616015

Reaction notes

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