Citric Acid → 4-cyclohexylamino-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde

HRID 1966810Notes

Reaction equation

HRID 1966810 reaction equation
COCCO[AlH2-]OCCOC.[Na+].[CH:13]1([NH:19][C:20]2[C:25]([C:26](N(OC)C)=[O:27])=[CH:24][N:23]=[C:22]3[N:32]([CH2:35][CH3:36])[N:33]=[CH:34][C:21]=23)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1(C)C=CC=CC=1>[CH:13]1([NH:19][C:20]2[C:25]([CH:26]=[O:27])=[CH:24][N:23]=[C:22]3[N:32]([CH2:35][CH3:36])[N:33]=[CH:34][C:21]=23)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 16684438Red-AlHCID 251057824-(cyclohexylamino)-1-ethyl-N-methoxy-N-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxamide

Product 1

HCID 251057854-cyclohexylamino-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Toluene was cooled to −30 to −35° C. and vitride (0.12 ml, 0.0006 mole) was added. After about 10 min., 4-(cyclohexylamino)-1-ethyl-N-methoxy-N-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxamide (0.10 gm, 0.0003 mole) (example 6) was added and the reaction mixture was stirred for about 4 h. Citric acid (10%) solution was added dropwise to quench the reaction and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulphate and concentrated in vacuo. The compound was purified over preparative thin layer chromatography.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe compound was purified over preparative thin layer chromatography

Sources & evidence

ORD record
ord-c565c711aa5f4a1a91e11bc99dbc3f2a
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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