Sodium Azide → HCID 86640802, compound

HRID 2198123Notes

Reaction equation

HRID 2198123 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[N:14][CH:15]=[C:16]([C:17]([NH:19][C@H:20]([C:28]4[CH:33]=[CH:32][N:31]=[C:30]([S:34]([CH3:37])(=[O:36])=[O:35])[CH:29]=4)[CH2:21][CH2:22]OS(C)(=O)=O)=[O:18])[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[N-:38]=[N+:39]=[N-:40].[Na+]>CN(C=O)C>[N:38]([CH2:22][CH2:21][C@H:20]([NH:19][C:17]([C:16]1[C:11]2[CH:10]=[N:9][N:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:12]=2[CH:13]=[N:14][CH:15]=1)=[O:18])[C:28]1[CH:33]=[CH:32][N:31]=[C:30]([S:34]([CH3:37])(=[O:36])=[O:35])[CH:29]=1)=[N+:39]=[N-:40]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86640801HCID 86640801, compound

Product 1

HCID 86640802HCID 86640802, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a room temperature solution of methanesulfonic acid (S)-3-{[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-3-(2-methanesulfonyl-pyridin-4-yl)-propyl ester (122 mg, 0.223 mmol) in DMF (2 mL) was added sodium azide (19 mg, 0.29 mmol). After 72 hours, the reaction was quenched with water (20 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were washed with water (20 mL), brine (20 mL), dried over magnesium sulfate, filtered and concentrated. The mixture was passed through a plug of silica gel eluting with a gradient of 0-5% methanol in dichloromethane to afford 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [(S)-3-azido-1-(2-methanesulfonyl-pyridin-4-yl)-propyl]-amide which was used without further purification.

Workup

  1. customthe reaction was quenched with water (20 mL)
  2. extractionextracted with EtOAc (3×20 mL)
  3. washThe combined organic layers were washed with water (20 mL), brine (20 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a711df41ff844727b0606f9323839ab7
Source dataset
uspto-grants-2012_12
Patent number
US08338610B2

Reaction notes

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