Hydrochloric Acid → 3-Fluoro-4-[3-methyl-4-(2-phenyl-piperazin-1-ylmethyl)-1H-pyrazolo[3,4-b]pyridin-6-yl]-phenol

HRID 2279090Notes

Reaction equation

HRID 2279090 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=3[F:28])[N:18]=[C:17]3[N:29](C4CCCCO4)[N:30]=[C:31]([CH3:32])[C:16]=23)[CH:10]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[F:28][C:22]1[CH:23]=[C:24]([OH:27])[CH:25]=[CH:26][C:21]=1[C:19]1[N:18]=[C:17]2[NH:29][N:30]=[C:31]([CH3:32])[C:16]2=[C:15]([CH2:14][N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]2[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1366231874-[6-(2-fluoro-4-hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl]-3-phenyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 1784344133-Fluoro-4-[3-methyl-4-(2-phenyl-piperazin-1-ylmethyl)-1H-pyrazolo[3,4-b]pyridin-6-yl]-phenolYield 51%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

178 mg 4-[6-(2-fluoro-4-hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl]-3-phenyl-piperazine-1-carboxylic acid tert-butyl ester were dissolved in 3 ml dry 1,4-dioxane and 2 ml HCl (4N in 1,4-dioxane) was added. After stirring the reaction at r.t. for 30 min the volatiles were removed in vacuo and the resulting residue was purified by preparative HPLC (C18 column, acetonitrile/water gradient). 63 mg (51%) of the title compound were obtained.

Workup

  1. customthe reaction at r.t. for 30 min the volatiles
  2. customwere removed in vacuo
  3. customthe resulting residue was purified by preparative HPLC (C18 column, acetonitrile/water gradient)

Sources & evidence

ORD record
ord-5f712bb02b6145ebafd89812ed0b31f4
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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