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

HRID 901172

Reaction equation

HRID 901172 reaction equation
[OH-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([F:33])=[C:22]([O:24]C(=O)C3C=CC=CC=3)[CH:23]=2)[N:12]2[CH:16]=[N:15][N:14]=[CH:13]2)=[CH:7][CH:6]=1)#[N:4]>O.CO>[F:33][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][N:11]([N:12]2[CH:13]=[N:14][N:15]=[CH:16]2)[C:8]2[CH:7]=[CH:6][C:5]([C:3]#[N:4])=[CH:10][CH:9]=2)=[CH:23][C:22]=1[OH:24]

Participants

5

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]triazole

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (250 mg, 6.25 mmol) in water (5 mL) was added to a solution of benzoic acid 5-{[(4-cyano-phenyl)-[1,2,4]triazol-4-yl-amino]methyl}-2-fluoro-phenyl ester (CAB02147, 958 mg, 2.32 mmol) in methanol (10 mL). The solution was heated to reflux for 5 minutes and concentrated under reduced pressure. Water (10 mL) was added and the milky suspension was neutralised (pH 7-8) with 2N hydrochloric acid. The white precipitate was filtered off, washed with a small amount of water (5 mL) and dried under high vacuum. Yield: 476 mg (66%). 1H-NMR (400 MHz, d6-DMSO) δ=4.95 (s, 2H), 6.70 (ddd, J=11.4, 8.4, 2.4 Hz, 1H), 6.75 (d, J=9.0 Hz, 2H), 6.84 (dd, J=8.4, 2.4 Hz, 1H), 7.06 (dd, J=11.3, 8.4 Hz, 1H), 7.76 (d, J=9.0 Hz, 2H), 8.75 (s, 2H), 9.90 (s, 1H, —OH). LRMS (FAB+): 310.1 (100, [M+H]+).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 5 minutes
  3. concentrationconcentrated under reduced pressure
  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-3fa8927c54b84c3f8a3b183cde8230a8
Source dataset
uspto-grants-2008_04
Patent number
US07361677B2

Linked notes

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