Sodium Methoxide → 4-[(4-Chloro-3-hydroxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole

HRID 1685654Notes

Reaction equation

HRID 1685654 reaction equation
C([O:9][C:10]1[CH:11]=[C:12]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:13][N:14]([C:20]1[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=1)[N:15]1[CH:19]=[N:18][N:17]=[CH:16]1)(=O)C1C=CC=CC=1.C[O-].[Na+]>CO.O>[Cl:31][C:30]1[CH:29]=[CH:28][C:12]([CH2:13][N:14]([C:20]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=2)[N:15]2[CH:16]=[N:17][N:18]=[CH:19]2)=[CH:11][C:10]=1[OH:9]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 167492234-[(3-benzoyloxy-4-chlorobenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole

Product 1

HCID 167492244-[(4-Chloro-3-hydroxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazoleYield 48.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-[(3-benzoyloxy-4-chlorobenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole (1.13 g, 2.63 mmol) and NaOMe (500 mg) in MeOH (20 mL) and water (5 mL) was heated to reflux for 30 minutes. After cooling to room temperature most of the solvent was removed in vacuo and concentrated sodium bicarbonate solution (20 mL) and EtOAc (50 mL) were added. The organic layer was separated, dried (Na2SO4) and the solvent was removed under reduced pressure. The resulting white powder was refluxed in EtOAc (10 mL, product did not dissolve completely). The product was filtered off and dried in vacuo to give STX483 as a white powder (0.412 g, 48%); δH (400 MHz, DMSO-d6) 4.97 (s, 2H), 6.71-6.75 (m, 3H, AA′BB′ and ArH), 6.84 (d, J=2.0, 1H), 7.25 (d, J=8.2, 1H), 7.75 (AA′BB′, 2H), 8.76 (s, 2H), 10.21 (s, 1H—exchanges with D2O); LRMS (FAB+) m/z (rel. intensity) 326.1 (100, [M+H]+).

Workup

  1. temperatureto reflux for 30 minutes
  2. customwas removed in vacuo and concentrated sodium bicarbonate solution (20 mL) and EtOAc (50 mL)
  3. additionwere added
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was removed under reduced pressure
  7. temperatureThe resulting white powder was refluxed in EtOAc (10 mL, product
  8. dissolutiondid not dissolve completely)
  9. filtrationThe product was filtered off
  10. customdried in vacuo

Sources & evidence

ORD record
ord-66cd4ee5e2f5498e9796c9c696ad21b4
Source dataset
uspto-grants-2012_04
Patent number
US08148415B2

Reaction notes

Loading…