HCID 69421897, compound → HCID 69420612, compound

HRID 1273009Notes

Reaction equation

HRID 1273009 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:25]([NH2:27])=[O:26])[CH:23]=3)[N:18](C3CCCCO3)[N:17]=2)[CH:13]=[CH:14][CH:15]=1>Cl.O1CCOCC1>[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:25]([NH2:27])=[O:26])[CH:23]=3)[NH:18][N:17]=2)[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 69421897HCID 69421897, compound

Product 1

HCID 69420612HCID 69420612, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

3-[3-(2-Piperidylethoxy)phenyl]-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carboxamide (0.61 g, 1.4 mmol) was suspended in 10 mL of 4 M HCl in dioxane and the suspension was stirred at room temperature for 18 h. The reaction was quenched with saturated aqueous solution of NaHCO3 and extracted with EtOAc. The organic layer was dried (Na2SO4) and filtered. The filtrate was concentrated and purification of the residue by preparative HPLC (20–80% acetonitrile in water) furnished 65 mg (13% yield) of the title compound. 1H NMR (DMSO-d6) δ 13.4 (br s, 1H), 8.6 (s, 1H), 8.2 (s, 1H), 7.94 (dd, 1H), 7.62 (m, 2H), 7.5 (m, 1H), 7.45 (t, 1H), 7.32 (br s, 1H), 7.05 (dd, 1H), 4.18 (t, 2H), 2.7 (m, 2H), 2.5 (m, 4H), 1.5 (m, 4H), 1.4 (m, 2H); ES-MS (m/z) 365 [M+H]+.

Workup

  1. customThe reaction was quenched with saturated aqueous solution of NaHCO3
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurification of the residue by preparative HPLC (20–80% acetonitrile in water)

Sources & evidence

ORD record
ord-1c5c1fb277774f50a66336f50903a720
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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