Formic Acid → HCID 68446158, compound

HRID 42605Notes

Reaction equation

HRID 42605 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]3[NH:14][N:15]=[CH:16][C:11]3=[C:10]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:9]=2[C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)=[CH:4][CH:3]=1.[OH-].[Na+].[CH:31](O)=O>C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]3[NH:14][N:15]=[CH:16][C:11]3=[C:10]([CH:17]3[CH2:18][CH2:19][N:20]([CH3:31])[CH2:21][CH2:22]3)[C:9]=2[C:23]2[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 68445265HCID 68445265, compound

Product 1

HCID 68446158HCID 68446158, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Conditions

Temperature
75 °C

Procedure

To a suspension of 6-(4-fluorophenyl)-4-(4-piperidyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine (0.24 g, 0.6 mmol, obtained in example 170) in formic acid (0.64 mL), 35-40% aqueous formaldehyde (0.96 mL) was added. It was heated to 70-80° C. for 24 h. It was allowed to cool and 1 N NaOH was added. It was extracted with CHCl3 and the combined organic phases were dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using CHCl3-MeOH—NH3 mixtures of increasing polarity as eluent, to afford 47 mg of the desired compound (yield: 19%).

Workup

  1. additionwas added
  2. temperatureto cool
  3. extractionIt was extracted with CHCl3
  4. dry with materialthe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe crude product obtained
  7. customwas purified by chromatography on silica gel
  8. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-10c4784e7d8e4503b51543c5623d2a75
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Reaction notes

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