HCID 68048507, compound → HCID 86683816, compound

HRID 1620317Notes

Reaction equation

HRID 1620317 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([O:6][C:7]2[CH:19]=[CH:18][C:10]([C:11]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[O:12])=[CH:9][C:8]=2[C:20]2[N:24](C3CCCCO3)[N:23]=[CH:22][CH:21]=2)=[CH:4][C:3]=1[CH2:33][CH3:34]>Cl.O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([O:6][C:7]2[CH:19]=[CH:18][C:10]([C:11]([NH:13][S:14]([CH3:17])(=[O:15])=[O:16])=[O:12])=[CH:9][C:8]=2[C:20]2[NH:24][N:23]=[CH:22][CH:21]=2)=[CH:4][C:3]=1[CH2:33][CH3:34]

Participants

4

Reactant 1

HCID 68048507HCID 68048507, compound

Product 1

HCID 86683816HCID 86683816, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

4-(4-chloro-3-ethylphenoxy)-N-(methylsulfonyl)-3-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)benzamide (Preparation 22, 335 mg, 0.53 mmol) was dissolved in 4M hydrogen chloride in dioxane (5 mL). The reaction mixture was stirred 3 hours then concentrated in vacuo. The crude residue was dissolved in methanol (5 mL) and 12N aqueous solution of hydrochloric acid (0.5 mL) was added. The reaction mixture was stirred for 18 hours at room temperature. The reaction mixture was concentrated to dryness then the residue was azeotroped with methanol (25 mL). The crude solid was triturated with tert-butyl methyl ether (4 mL) and the suspension was filtered off. The filtrate was washed with tert-butyl methyl ether to afford the title compound as a cream coloured solid (HCl salt, 106 mg, 44%).

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe crude residue was dissolved in methanol (5 mL)
  3. addition12N aqueous solution of hydrochloric acid (0.5 mL) was added
  4. stirringThe reaction mixture was stirred for 18 hours at room temperature
  5. concentrationThe reaction mixture was concentrated to dryness
  6. customthe residue was azeotroped with methanol (25 mL)
  7. customThe crude solid was triturated with tert-butyl methyl ether (4 mL)
  8. filtrationthe suspension was filtered off
  9. washThe filtrate was washed with tert-butyl methyl ether

Sources & evidence

ORD record
ord-ad5bf567db8f4279aa80c1791fbdca68
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

Loading…