Hydrochloric Acid → HCID 178434389, compound

HRID 2279144Notes

Reaction equation

HRID 2279144 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][C:32]([CH3:35])([CH3:34])[N:31]([CH2:36][CH2:37][C:38]([F:41])([F:40])[F:39])[CH2:30][C:29]3([CH3:43])[CH3:42])[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:9]=[CH:10][C:5]([OH:4])=[CH:6][CH:7]=3)=[CH:12][C:13]=2[CH2:27][N:28]2[CH2:33][C:32]([CH3:34])([CH3:35])[N:31]([CH2:36][CH2:37][C:38]([F:41])([F:40])[F:39])[CH2:30][C:29]2([CH3:43])[CH3:42])[NH:17][N:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90013829HCID 90013829, compound

Product 1

HCID 178434389HCID 178434389, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

167 mg of 6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-4-[2,2,5,5-tetramethyl-4-(3,3,3-trifluoro-propyl)-piperazin-1-ylmethyl]-1H-pyrazolo[3,4-b]pyridine were dissolved in 2 ml of 1,4-dioxane and treated with 1.5 ml of hydrochloric acid (4M in dry dioxane). After standing at rt for 16 h the volatiles were removed in vacuo. The residue was purified by preparative HPLC (C18 column, acetonitrile/water gradient) and 62 mg (47%) 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-e20811f3b81846faa1a90aec54eabdce
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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