Citric Acid → HCID 86636866, compound

HRID 606029Notes

Reaction equation

HRID 606029 reaction equation
COCCO[AlH2-]OCCOC.[Na+].[CH:13]1([NH:16][C:17]2[C:22]([C:23](N(OC)C)=[O:24])=[CH:21][N:20]=[C:19]3[N:29]([CH2:32][CH3:33])[N:30]=[CH:31][C:18]=23)[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:16][C:17]2[C:22]([CH:23]=[O:24])=[CH:21][N:20]=[C:19]3[N:29]([CH2:32][CH3:33])[N:30]=[CH:31][C:18]=23)[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 16684438Red-AlHCID 86636865HCID 86636865, compound

Product 1

HCID 86636866HCID 86636866, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Toluene was cooled at −19 to −20° C. and vitride (0.50 ml, 0.0034 mole) was added. After about 10 minutes, 4-(cyclopropylamino)-1-ethyl-N-methoxy-N-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxamide (500 mg, 0.0017 mole) was added and the reaction mixture was stirred for about 4 hours. 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 sulfate and concentrated in vacuo to give an oily compound. Yield: 300 mg. m/z: (M++1) 231.1.

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 sulfate
  6. concentrationconcentrated in vacuo
  7. customto give an oily compound

Sources & evidence

ORD record
ord-b7bcd8f51ec84d03bf2f06efcd1dcfc0
Source dataset
uspto-grants-2011_03
Patent number
US07915286B2

Reaction notes

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