Hydrochloric Acid → HCID 67959686, compound

HRID 1529325Notes

Reaction equation

HRID 1529325 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[C:22]([O:24][CH3:25])[CH:23]=4)[CH:16]=3)[N:11](C3CCCCO3)[N:10]=2)[CH:6]=[N:7][CH:8]=1.Cl.CC(O)C>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[C:22]([O:24][CH3:25])[CH:23]=4)[CH:16]=3)[NH:11][N:10]=2)[CH:6]=[N:7][CH:8]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 67959598HCID 67959598, compound

Product 1

HCID 67959686HCID 67959686, compound

Conditions

Temperature
50 °C

Procedure

A mixture of 3,5-bis(5-methoxypyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (0.429 g, 1.029 mmol) and HCl, 5-6 N in IPA (10 mL, 50.0 mmol) was heated at 50° C. for 2.5 h. The reaction was cooled to RT and the solvent was removed in vacuo. The material was basified with 5 N NaOH and diluted with MeOH. The solution was purified by reverse-phase HPLC (Gilson; Gemini-NX 14, C18 110 A AXIA, 100×50 mm column) eluting with 0.1% TFA-H2O:0.1% TFA ACN (9:1→1:9). The fractions containing the desired product were combined and concentrated in vacuo to give a white crystalline solid. m/z: 333.2 (M+1).

Workup

  1. temperatureThe reaction was cooled to RT
  2. customthe solvent was removed in vacuo
  3. additiondiluted with MeOH
  4. customThe solution was purified by reverse-phase HPLC (Gilson
  5. washGemini-NX 14, C18 110 A AXIA, 100×50 mm column) eluting with 0.1% TFA-H2O
  6. additionThe fractions containing the desired product
  7. concentrationconcentrated in vacuo
  8. customto give a white crystalline solid

Sources & evidence

ORD record
ord-a705fffcc5ea47e38d866cfc3f66703f
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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