HCID 22609893, compound → HCID 22609913, compound

HRID 1369427Notes

Reaction equation

HRID 1369427 reaction equation
[CH:1]1([C:5]2[C:10]([O:11][CH2:12][C:13]3[N:17](COCC[Si](C)(C)C)[C:16]4[CH:26]=[CH:27][CH:28]=[CH:29][C:15]=4[N:14]=3)=[N:9][N:8]3[C:30]([C:33]4[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:34]=4[F:40])=[N:31][N:32]=[C:7]3[CH:6]=2)[CH2:4][CH2:3][CH2:2]1>Cl.C(O)C>[NH:17]1[C:16]2[CH:26]=[CH:27][CH:28]=[CH:29][C:15]=2[N:14]=[C:13]1[CH2:12][O:11][C:10]1[C:5]([CH:1]2[CH2:2][CH2:3][CH2:4]2)=[CH:6][C:7]2[N:8]([C:30]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:34]=3[F:40])=[N:31][N:32]=2)[N:9]=1

Participants

4

Reactant 1

HCID 22609893HCID 22609893, compound

Product 1

HCID 22609913HCID 22609913, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 7-cyclobutyl-3-(2,4-difluorophenyl)-6-[1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-ylmethoxy]-1,2,4-triazolo[4,3-b]pyridazine (187 mg, 0.333 mmol) in 5M hydrochloric acid (10 ml) and ethanol (4 ml) was heated at 80° C. overnight, then concentrated in vacuo to remove solvents. Saturated potassium carbonate solution was added, then the mixture was diluted with water, filtered and the residual solid washed with water then ether and then dried. The residue was purified by flash chromatography on silica gel using ethyl acetate as eluent to give the title compound (60 mg, 42%). Data for the title compound: 1H NMR (250 MHz, CDCl3) δ10.62 (1H, br s), 7.85 (2H, m), 7.56 (1H, d, J 1.6 Hz), 7.48 (1H, br s), 7.32 (2H, m), 7.00 (2H, m), 5.65 (2H, s), 3.54 (1H, m), 2.24 (2H, m), 2.01 (3H, m). 1.80 (1H, m); MS (ES+) m/e 433 [MH]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove solvents
  3. additionSaturated potassium carbonate solution was added
  4. additionthe mixture was diluted with water
  5. filtrationfiltered
  6. washthe residual solid washed with water
  7. dry with materialether and then dried
  8. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-1a2c3f7d8db74062915b3e7acd713081
Source dataset
uspto-grants-2003_06
Patent number
US06579875B1

Reaction notes

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