Triethylamine → Ethyl 2-[({1-[(3,4-dichlorophenyl)methyl]-5-methyl-1h-1,2,3-triazol-4-yl}carbonyl)amino]-1,3-oxazole-5-carboxylate

HRID 222366Notes

Reaction equation

HRID 222366 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([OH:18])=O)[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[NH2:19][C:20]1[O:21][C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][N:24]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CCN(CC)CC>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([NH:19][C:20]3[O:21][C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][N:24]=3)=[O:18])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2×HCID 757711-Hydroxybenzotriazole2×HCID 5260193Ethyl 2-amino-1,3-oxazole-5-carboxylateHCID 550298731-(3,4-dichlorobenzyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid2×

Product 1

HCID 59583669Ethyl 2-[({1-[(3,4-dichlorophenyl)methyl]-5-methyl-1h-1,2,3-triazol-4-yl}carbonyl)amino]-1,3-oxazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (Intermediate 4) (1 g, 3.4 mmol), ethyl 2-amino-1,3-oxazole-5-carboxylate (0.82 g, 5.2 mmol), HOBt (0.708 g, 5.2 mmol), EDCI (1.005 g, 5.2 mmol) and NEt3 (730 μL, 5.2 mmol) in DMF (50 mL) was stirred at room temperature for 2 days. The reaction was not completed and 2.5 eq of EDCI and HOBt were added and the reaction was heated at 40° C. and stirred for a further 14 days. Again no completed reaction was obtained. The solvent was evaporated and the residue was washed with water and extracted with DCM. The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography eluting with DCM/MeOH (90/10) to give after crystallisation from diisopropyl ether, the title compound as a yellow solid (98 mg, 6%). LC/MS: m/z 424 (M+H)+. Rt: 3.17 min.

Workup

  1. temperaturethe reaction was heated at 40° C.
  2. stirringstirred for a further 14 days
  3. customAgain no completed reaction
  4. customwas obtained
  5. customThe solvent was evaporated
  6. washthe residue was washed with water
  7. extractionextracted with DCM
  8. dry with materialThe organic phase was dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by flash column chromatography
  12. washeluting with DCM/MeOH (90/10)
  13. customto give
  14. customafter crystallisation from diisopropyl ether

Sources & evidence

ORD record
ord-1460b74d06634048a94326d0f558edc7
Source dataset
uspto-grants-2012_06
Patent number
US08207204B2

Reaction notes

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