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Water → 6-(4-Hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (1-benzyl-4-methyl-piperidin-4-yl)-amide

HRID 2360688
Notes
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Reaction equation

HRID 2360688 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:24]([OH:26])=O)[C:11]3[C:16]([CH3:17])=[N:15][N:14]([CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][O:19]4)[C:12]=3[N:13]=2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH2:36]([N:43]1[CH2:48][CH2:47][C:46]([NH2:50])([CH3:49])[CH2:45][CH2:44]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.O>ClC(Cl)C>[CH2:36]([N:43]1[CH2:48][CH2:47][C:46]([NH:50][C:24]([C:10]2[C:11]3[C:16]([CH3:17])=[N:15][N:14]([CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][O:19]4)[C:12]=3[N:13]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=3)[CH:9]=2)=[O:26])([CH3:49])[CH2:45][CH2:44]1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 221467251-Benzyl-4-methylpiperidin-4-amineHCID 1363597706-(4-Hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 1363597716-(4-Hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (1-benzyl-4-methyl-piperidin-4-yl)-amide
Yield 432,469.312%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 6-(4-hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (215 mg), DIPEA (313 μL) and 1-benzyl-4-methyl-piperidin-4-ylamine (175 mg) in dichloroethane (7 mL), which was being stirred at 40° C., was added BEP (200 mg). The mixture was stirred at 40° C. for 60 min, then at r.t. overnight. Water was added and the mixture was extracted with dichloromethane. To the dichloromethane phase 30% sodium methoxide in methanol (0.4 mL) was added and stirred for 30 min. The mixture was filtered and the filtrate was washed with water, dried over magnesium sulfate and concentrated. The residue was chromatographed over silica (dichloromethane/methanol gradient) to give 1420 g (43%) of the title compound.

Workup

  1. additionwas added BEP (200 mg)
  2. stirringThe mixture was stirred at 40° C. for 60 min
  3. customat r.t.
  4. customovernight
  5. extractionthe mixture was extracted with dichloromethane
  6. additionTo the dichloromethane phase 30% sodium methoxide in methanol (0.4 mL) was added
  7. stirringstirred for 30 min
  8. filtrationThe mixture was filtered
  9. washthe filtrate was washed with water
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated
  12. customThe residue was chromatographed over silica (dichloromethane/methanol gradient)

Sources & evidence

ORD record
ord-7cfa41e362724d25b5e57a1ed18271f2
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08686150B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes