Hydrochloric Acid → HCID 178434393, compound

HRID 2279158Notes

Reaction equation

HRID 2279158 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]3[N:17](C4CCCCO4)[N:18]=[C:19]([CH3:20])[C:14]3=[C:13]([CH2:27][N:28]3[CH2:33][CH2:32][NH:31][C@H:30]([CH2:34][C:35]([F:38])([F:37])[F:36])[CH2:29]3)[CH:12]=2)=[CH:7][CH:6]=1.Cl>O1CCOCC1>[CH3:20][C:19]1[C:14]2[C:15](=[N:16][C:11]([C:8]3[CH:7]=[CH:6][C:5]([OH:4])=[CH:10][CH:9]=3)=[CH:12][C:13]=2[CH2:27][N:28]2[CH2:33][CH2:32][NH:31][C@H:30]([CH2:34][C:35]([F:38])([F:37])[F:36])[CH2:29]2)[NH:17][N:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90013594HCID 90013594, compound

Product 1

HCID 178434393HCID 178434393, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

188 mg of 6-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-4-[(R)-3-(2,2,2-trifluoro-ethyl)-piperazin-1-ylmethyl]-1H-pyrazolo[3,4-b]pyridine were dissolved in 2 ml of 1,4-dioxane and treated with 2 ml of hydrochloric acid (4M in dry dioxane). After standing at rt for 1.5 h the volatiles were removed in vacuo. The residue was purified by preparative HPLC (C18 column, acetonitrile/water gradient) and 73 mg (50%) of the title compound were obtained.

Workup

  1. customthe volatiles were removed in vacuo
  2. customThe residue was purified by preparative HPLC (C18 column, acetonitrile/water gradient)

Sources & evidence

ORD record
ord-5bada0302c634e56bf3cc6a686563492
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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