2-Methyl-2-butene → HCID 66727356, compound

HRID 1698148Notes

Reaction equation

HRID 1698148 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[C:9]([C@@H:11]([NH:15][C:16]([C:18]2[C:19]3[CH:26]=[N:25][N:24]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[C:20]=3[CH:21]=[N:22][CH:23]=2)=[O:17])[CH2:12][CH:13]=[O:14])[CH:8]=[CH:7][N:6]=1)(=[O:4])=[O:3].CC(=CC)C.Cl([O-])=[O:40].[Na+].O.P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C.O>[F:33][C:30]1[CH:29]=[CH:28][C:27]([N:24]2[C:20]3[CH:21]=[N:22][CH:23]=[C:18]([C:16]([NH:15][C@H:11]([C:9]4[CH:8]=[CH:7][N:6]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:10]=4)[CH2:12][C:13]([OH:40])=[O:14])=[O:17])[C:19]=3[CH:26]=[N:25]2)=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 59278338HCID 59278338, compound

Product 1

HCID 66727356HCID 66727356, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a room temperature solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [(S)-1-(2-methanesulfonyl-pyridin-4-yl)-3-oxo-propyl]-amide (0.10 g, 0.21 mmol) and 2-methyl-2-butene (147 μL, 1.39 mmol) in t-butanol (1 mL) was added a solution of 80% sodium chlorite (31 mg, 0.28 mmol) and sodium dihydrogen phosphate monohydrate (38 mg, 0.28 mmol) in water (400 μL) (addition was exothermic). The mixture stirred overnight and was then concentrated in vacuo, acidified with 1 N aqueous HCl (pH=2), diluted with brine (25 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to afford (S)-3-{[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-3-(2-methanesulfonyl-pyridin-4-yl)-propionic acid which was used without further purification.

Workup

  1. concentrationwas then concentrated in vacuo
  2. additiondiluted with brine (25 mL)
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9696ca4e077b433d84bb5c25bb95b808
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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