Hydrochloric Acid → HCID 22480119, compound

HRID 1349649Notes

Reaction equation

HRID 1349649 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[N:19])[CH:16]=3)[N:11](C3CCCCO3)[N:10]=2)=[CH:5][CH:4]=1.O1CCOCC1.Cl.O>CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[N:19])[CH:16]=3)[NH:11][N:10]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 312751,4-DioxaneHCID 22479756HCID 22479756, compound

Product 1

HCID 22480119HCID 22480119, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 251 mg (0.753 mmol) of 3-(4-methoxyphenyl)-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile, 5.0 mL of dioxane, and 5.0 mL of 6.0 N aq. HCl was heated at 65° C. for 22 h. The reaction mixture was added to a mixture of 10.0 mL of H2O and 20.0 mL of EtOAc with stirring. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were added to 60 mL of sat. aq. NaHCO3 with rapid stirring. The layers were separated, and the organic layer was washed with sat. aq. NaHCO3, and dried (Na2SO4). Purification of the crude material by silica gel chromatography using 30–50% EtOAc in hexanes afforded the title compound (129 mg, 71% yield): ES-MS (m/z) 250 [M+1]+.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. additionThe combined organic layers were added to 60 mL of sat. aq. NaHCO3 with rapid stirring
  4. customThe layers were separated
  5. washthe organic layer was washed with sat. aq. NaHCO3
  6. dry with materialdried (Na2SO4)
  7. customPurification of the crude material by silica gel chromatography

Sources & evidence

ORD record
ord-45ec32a392cb4bd0876594fc3143de4e
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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