Hydrochloric Acid → HCID 71253902, compound

HRID 1774996Notes

Reaction equation

HRID 1774996 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:15]3[C:10](=[CH:11][N:12]=[C:13]([C:16]4[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=4)[CH:14]=3)[N:9](C3CCCCO3)[N:8]=2)[CH:4]=[N:3]1.Cl>CO.O1CCOCC1>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:15]3[C:10](=[CH:11][N:12]=[C:13]([C:16]4[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=4)[CH:14]=3)[NH:9][N:8]=2)[CH:4]=[N:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71253559HCID 71253559, compound

Product 1

HCID 71253902HCID 71253902, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

3,5-bis(1-methyl-1H-pyrazol-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine in methanol was treated with 4M HCl in 1,4-dioxane at 50° C. for 3 h. Volatile solvent was evaporated in vacuo. The resultant residue was purified by reverse phase HPLC to give 163 as a white solid (34.2%). 1H NMR (500 MHz, DMSO) δ 13.35 (s, 1H), 8.96 (s, 1H), 8.47 (s, 1H), 8.29 (s, 1H), 8.15 (s, 1H), 8.10 (d, J=5.6 Hz, 2H), 3.96 (s, 3H), 3.90 (s, 3H). LC/MS: m/z 280.0 [M+1]

Workup

  1. customVolatile solvent was evaporated in vacuo
  2. customThe resultant residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-dfc01439218a44e99903d2dc21b34961
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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