Hydrochloric Acid → HCID 67527941, compound

HRID 2261749Notes

Reaction equation

HRID 2261749 reaction equation
Cl.O1CCOCC1.C(O[C:13](=O)[N:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[N:25]([C:32]3[C:37]([Cl:38])=[CH:36][CH:35]=[CH:34][C:33]=3[Cl:39])[N:26]=[CH:27][C:28]=2[CH:29]([CH3:31])[CH3:30])=[CH:18][C:17]=1[CH3:40])C)(C)(C)C>ClCCl>[Cl:38][C:37]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:39])[C:32]=1[N:25]1[C:24]([CH2:23][O:22][C:19]2[CH:20]=[CH:21][C:16]([NH:14][CH3:13])=[C:17]([CH3:40])[CH:18]=2)=[C:28]([CH:29]([CH3:31])[CH3:30])[CH:27]=[N:26]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67528435HCID 67528435, compound

Product 1

HCID 67527941HCID 67527941, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.0 M HCl in 1,4-dioxane (2.8 mL, 11.0 mmol) is added to a solution of {4-[2-(2,6-dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-methyl-carbamic acid tert-butyl ester (1.85 g, 3.7 mmol) in dichloromethane (25.0 mL) at 0° C. The reaction mixture is then stirred at room temperature for 2.0 h. The solvents are removed by evaporation under reduced pressure. The residue is partitioned between EtOAc (50 mL) and 5% aqueous sodium bicarbonate (30 mL). The organic layer is washed with brine (40 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography (EtOAc/Hexane) to afford the title compound as a foamy solid (1.25 g, 84%). LC-ES/MS m/e 404.0 (M+1).

Workup

  1. customThe solvents are removed by evaporation under reduced pressure
  2. customThe residue is partitioned between EtOAc (50 mL) and 5% aqueous sodium bicarbonate (30 mL)
  3. washThe organic layer is washed with brine (40 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to a residue
  7. customThe residue is purified by flash chromatography (EtOAc/Hexane)

Sources & evidence

ORD record
ord-e74e167c43f34d59a2a74db8b1296a82
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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