1-Hydroxybenzotriazole → HCID 68983388, compound

HRID 475564Notes

Reaction equation

HRID 475564 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:17]2[O:18][CH:19]=[C:20]([CH2:22][NH2:23])[N:21]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH3:46][C:47]1[C:48]([C:53](O)=[O:54])=[N:49][CH:50]=[CH:51][CH:52]=1>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:17]2[O:18][CH:19]=[C:20]([CH2:22][NH:23][C:53](=[O:54])[C:48]3[C:47]([CH3:46])=[CH:52][CH:51]=[CH:50][N:49]=3)[N:21]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 2687573-Methylpicolinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68981656HCID 68981656, compound

Product 1

HCID 68983388HCID 68983388, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 1.5 g quantity of the [2-(3-benzyloxy-4-methoxy phenyl)oxazol-4-yl]methylamine obtained in Reference Example 7 was suspended in 30 ml of acetone. To the obtained suspension were added 1.0 g of 1-hydroxybenzotriazole, 1.4 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 0.8 g of 3-methylpicolinic acid, and the mixture was heated and refluxed for 30 minutes. The reaction mixture was cooled, and acetone was distilled off under reduced pressure. Water was added to the residue, and extraction was then performed with ethyl acetate. The organic layer was washed with water twice, and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1) to give 1.5 g of white powdery N-[2-(3-benzyloxy-4-methoxyphenyl)oxazol-4-ylmethyl]-3-methylpicolinamide.

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 30 minutes
  3. temperatureThe reaction mixture was cooled
  4. distillationacetone was distilled off under reduced pressure
  5. additionWater was added to the residue, and extraction
  6. washThe organic layer was washed with water twice
  7. concentrationthe solvent was concentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-6c8ae42b9456404392f78f6f0a47e7b9
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

Loading…