Sulfuric Acid → HCID 66634913, compound

HRID 510100Notes

Reaction equation

HRID 510100 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:19]=[C:18]([NH2:20])[C:17]([NH2:21])=[CH:16][CH:15]=2)=[N:6]1.[CH3:26][CH:27]([CH3:35])[C:28](=O)[C:29](OCC)=[O:30].S(=O)(=O)(O)O>C(O)C>[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[CH:15]=[CH:16][C:17]3[N:21]=[C:28]([CH:27]([CH3:35])[CH3:26])[C:29](=[O:30])[NH:20][C:18]=3[N:19]=2)=[N:6]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 88406Ethyl 3-methyl-2-oxobutyrateHCID 666140516-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyridine-2,3-diamine

Product 1

HCID 66634913HCID 66634913, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

146 mg (0.435 mmol) of the compound from example 43A were initially charged in ethanol (8 ml), then 69 mg (0.48 mmol) of ethyl 3-methyl-2-oxobutanoate were added and the reaction mixture was heated to reflux overnight. Thereafter, a catalytic amount of conc. sulfuric acid was added and the mixture was again heated to reflux overnight. Subsequently, the mixture was cooled to RT, and the solid formed was filtered off, washed with methanol and dried under high vacuum. This gave 26 mg (14% of theory) of the title compound in solid form.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux overnight
  3. temperaturethe mixture was again heated
  4. temperatureto reflux overnight
  5. customthe solid formed
  6. filtrationwas filtered off
  7. washwashed with methanol
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-0189852fc78542d9908c6c603d0df4d4
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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