Water → HCID 9824172, compound

HRID 985420Notes

Reaction equation

HRID 985420 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([O:25]S(C2C=CC(C)=CC=2)(=O)=O)=[N:10][N:11]2[C:16]=1[C:15]([CH3:17])=[N:14][N:13]=[C:12]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:24].[CH3:36][N:37]1[C:41]([CH2:42]O)=[N:40][CH:39]=[N:38]1.[H-].[Na+].O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([O:25][CH2:42][C:41]2[N:37]([CH3:36])[N:38]=[CH:39][N:40]=2)=[N:10][N:11]2[C:16]=1[C:15]([CH3:17])=[N:14][N:13]=[C:12]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:24]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 11073377(1-methyl-1H-1,2,4-triazol-5-yl)methanolHCID 86587504HCID 86587504, compound

Product 1

HCID 9824172HCID 9824172, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To toluene-4-sulfonic acid 3,7-bis(2-fluorophenyl)-4-methylpyrazolo[1,5-d][1,2,4]triazin-2-yl ester (200 mg, 0.407 mmol) and (2-methyl-2H-[1,2,4]triazol-3-yl)methanol (57.5 mg, 0.0509 mmol; prepared as described in EP-A-170073) in DMF (5 ml) was added sodium hydride (23.7 mg of a 60% dispersion in mineral oil; 0.593 mmol) and the mixture was stirred at room temperature for 30 min. Water (50 ml) was added, then the solvent was removed in vacuo, and the residue was purified by flash chromatography on silica gel eluting with 0 to 100% ethyl acetate in dichloromethane. 3,7-Bis(2-fluorophenyl)-4-methyl-2-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)pyrazolo[1,5-d][1,2,4]triazine was isolated as a gum, which solidified upon trituration under isohexane (75 mg). 1H NMR (400 MHz, CDCl3) δ 2.52 (3H, s), 3.73 (3H, s), 5.44 (1H, d, J=13 Hz), 5.49 (1H, d, J=13 Hz), 7.18-7.31 (3H, m), 7.36-7.46 (3H, m), 7.63 (1H, m), 7.78 (1H, m), 7.82 (1H, s); MS (ES+) m/e 434 [MH]+. Anal. Found C, 61.03; H, 4.08; N, 21.95%. C22H17F2N7O.0.1 C6H14 requires C, 61.41; H, 4.20; N, 22.18%.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography on silica gel eluting with 0 to 100% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-231d2f74cba24f6d894fecf93044b14d
Source dataset
uspto-grants-2005_03
Patent number
US06872720B2

Reaction notes

Loading…