HCID 57411801, compound → HCID 57411803, compound

HRID 2046179Notes

Reaction equation

HRID 2046179 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][N:11]3[N:14]=[C:15]([CH2:17][O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[N:16]=[C:10]3[C:9]2=[O:25])=[CH:4][CH:3]=1>C(Cl)Cl.CO.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]3[N:14]=[C:15]([CH2:17][O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[N:16]=[C:10]3[C:9]2=[O:25])=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 57411801HCID 57411801, compound

Product 1

HCID 57411803HCID 57411803, compoundYield 6.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 7-(4-fluoro-phenyl)-2-phenoxymethyl-7H-[1,2,4]triazolo[1,5-a]pyrazin-8-one (26 mg, 0.08 mmol) in a mixture of DCM (1 mL) and MeOH (1 mL) was hydrogenated in a H-Cube reactor (1.0 mL/min, 30 mm Pd/C 10% cartridge, full H2 mode, 100° C., 3 cycles). The solvent was evaporated in vacuo and the residue was purified by RP HPLC, mobile phase (gradient from 80% 0.1% NH4CO3H pH=7.8 solution in H2O, 20% MeOH to 0% 0.1% NH4CO3H pH=7.8 solution in H2O, 100% MeOH) to yield 7-(4-fluoro-phenyl)-2-phenoxymethyl-6,7-dihydro-5H-[1,2,4]triazolo[1,5-a]pyrazin-8-one (1.7 mg, 6% yield). 1H NMR (400 MHz, CDCl3) δ ppm 4.11-4.24 (m, 2H), 4.44-4.58 (m, 2H), 5.42 (s, 2H), 6.95-7.02 (m, 2H), 7.04 (t, J=7.4 Hz, 1H), 7.13 (t, J=8.6 Hz, 2H), 7.29-7.49 (m, 4H).

Workup

  1. customwas hydrogenated in a H-Cube reactor
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was purified by RP HPLC, mobile phase (gradient from 80% 0.1% NH4CO3H pH=7.8 solution in H2O, 20% MeOH to 0% 0.1% NH4CO3H pH=7.8 solution in H2O, 100% MeOH)

Sources & evidence

ORD record
ord-ccc434409c814bb6aac1f0d93aa0c5e4
Source dataset
uspto-grants-2013_11
Patent number
US08592422B2

Reaction notes

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