Water → HCID 18406895, compound

HRID 1016413Notes

Reaction equation

HRID 1016413 reaction equation
[CH2:1]([N:3]1[C:7]([CH2:8][OH:9])=[N:6][CH:5]=[N:4]1)[CH3:2].[H-].[Na+].[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[C:20](OS(C2C=CC(C)=CC=2)(=O)=O)=[N:21][N:22]2[C:27]=1[CH:26]=[N:25][N:24]=[C:23]2[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[F:34].O>CN(C)C=O>[CH2:1]([N:3]1[C:7]([CH2:8][O:9][C:20]2[C:19]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[F:12])=[C:27]3[N:22]([C:23]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[F:34])=[N:24][N:25]=[CH:26]3)[N:21]=2)=[N:6][CH:5]=[N:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydride2×HCID 11412385(1-ethyl-1H-1,2,4-triazol-5-yl)methanolHCID 18406953HCID 18406953, compound

Product 1

HCID 18406895HCID 18406895, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The title compound was prepared as part of a rapid analogue library using the following methodology. To a solution of (2-ethyl-2H-[1,2,4]triazol-3-yl)methanol (32 mg, 0.25 mmol) in dry N,N-dimethylformamide (5 ml) in a RADLEYS reaction carousel under nitrogen was added sodium hydride (60% wt in oil) (10 mg, 0.25 mmol) and the suspension was stirred for 30 min. A solution of 3,7-bis(2-fluorophenyl)-2-(p-toluenesulfonyloxy)pyrazolo[1,5-d][1,2,4]triazine (100 mg, 0.21 mmol) in dry N,N-dimethylformamide (2 ml) was then added and the solution was stirred under nitrogen for 1 h. A further amount (4 mg, 0.10 mmol) of sodium hydride (60% wt in oil) was added and the solution was stirred for 18 h. Water (25 ml) was added to quench the reaction and the solid which was precipitated was collected by filtration and washed with water. The solid was dissolved in dichloromethane, filtered and the filtrate was concentrated in vacuo to give a white solid (40 mg). Data for the title compound: mp=164° C.; 1H NMR (360 MHz, CDCl3) δ 1.31 (3H, t), 4.09-4.16 (2H, m), 5.56 (2H, s), 7.21-7.33, (3H, m), 7.37-7.43 (2H, m), 7.58-7.68 (2H, m), 7.82 (1H, m), 7.87 (1H, s), 9.28 (1H, s); MS (ES+) m/e 434 [MH]+; HPLC>97% purity (run on an HP1100, using a Hichrom KR100-5C18, 25 cm column, flow rate of 1 ml/min and 50% acetonitrile/pH 3 phosphate buffer as the mobile phase).

Workup

  1. stirringthe solution was stirred under nitrogen for 1 h
  2. stirringthe solution was stirred for 18 h
  3. customto quench
  4. customthe reaction
  5. customthe solid which was precipitated
  6. filtrationwas collected by filtration
  7. washwashed with water
  8. dissolutionThe solid was dissolved in dichloromethane
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b1a775fe43514498b13fc1830cf450b3
Source dataset
uspto-grants-2002_11
Patent number
US06476030B1

Reaction notes

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