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

HRID 1685649Notes

Reaction equation

HRID 1685649 reaction equation
C([O:9][C:10]1[CH:11]=[C:12]([CH:28]=[CH:29][C:30]=1[F: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.[OH-].[Na+]>CO>[F: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

4

Reactant 2

HCID 14798Sodium HydroxideHCID 167492214-[(3-benzoyloxy-4-fluorobenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole

Product 1

HCID 167478394-[(4-Fluoro-3-hydroxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazoleYield 66.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[(3-benzoyloxy-4-fluorobenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole (0.958 g, 2.32 mmol) in MeOH (10 mL) was added NaOH (0.25 g, 6.25 mmol), and the solution heated to reflux for 5 minutes and then concentrated in vacuo. Water (10 mL) was added and the milky suspension was neutralised (pH 7-8) with 2N HCl. The white precipitate was filtered off, washed with a small amount of water (5 mL) and dried under high vacuum to give STX488 as a white solid (0.476 g, 66%); δH (400 MHz, DMSO-d6) 4.95 (s, 2H), 6.70 (ddd, J=11.4, 8.4, 2.4, 1H), 6.75 (AA′BB′, 2H), 6.84 (dd, J=8.4, 2.4, 1H), 7.06 (dd, J=11.3, 8.4, 1H), 7.76 (AA′BB′, 2H), 8.75 (s, 2H), 9.90 (s, 1H—exchanges with D2O); LRMS (FAB+) m/z (rel. intensity) 310.1 (100, [M+H]+).

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux for 5 minutes
  3. concentrationconcentrated in vacuo
  4. additionWater (10 mL) was added
  5. filtrationThe white precipitate was filtered off
  6. washwashed with a small amount of water (5 mL)
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-83339c7f50f947eaaed462f99c38f72a
Source dataset
uspto-grants-2012_04
Patent number
US08148415B2

Reaction notes

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