Sulfuric Acid → N-(5-Carbamoylpyrimidin-4-yl)-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxamide

HRID 510048Notes

Reaction equation

HRID 510048 reaction equation
[C:1]([C:3]1[C:4]([NH:9][C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[N:13]=2)=[O:11])=[N:5][CH:6]=[N:7][CH:8]=1)#[N:2].S(=O)(=O)(O)[OH:30]>>[C:1]([C:3]1[C:4]([NH:9][C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[N:13]=2)=[O:11])=[N:5][CH:6]=[N:7][CH:8]=1)(=[O:30])[NH2:2]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 66614381N-(5-Cyanopyrimidin-4-yl)-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxamide

Product 1

HCID 66614289N-(5-Carbamoylpyrimidin-4-yl)-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxamide

Procedure

581 mg (1.56 mmol) of the compound from example 47A were introduced in portions at 0° C. into conc. sulfuric acid (2.0 ml) and the mixture was stirred for a further 30 min. Subsequently, the solution was added to ice and extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated. The residue was stirred with ethyl acetate, and the solids were filtered off and dried under high vacuum. This gave 246 mg (40% of theory) of the title compound in solid form.

Workup

  1. additionSubsequently, the solution was added to ice
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. stirringThe residue was stirred with ethyl acetate
  7. filtrationthe solids were filtered off
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-ea55787f54f04a63a2338479d4d02118
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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