Dimethylformamide → HCID 178456076, compound

HRID 559644Notes

Reaction equation

HRID 559644 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([C@@H:9]([NH:12][C:13]([C:15]2[C:16]3[CH:23]=[N:22][N:21]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[C:17]=3[CH:18]=[N:19][CH:20]=2)=[O:14])[CH2:10][CH3:11])[CH:6]=[CH:5][N:4]=1)#[N:2].[N-:31]=[N+:32]=[N-:33].[Na+].CN(C=O)C>C(#N)C.O>[NH:31]1[C:1]([C:3]2[CH:8]=[C:7]([C@@H:9]([NH:12][C:13]([C:15]3[C:16]4[CH:23]=[N:22][N:21]([C:24]5[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=5)[C:17]=4[CH:18]=[N:19][CH:20]=3)=[O:14])[CH2:10][CH3:11])[CH:6]=[CH:5][N:4]=2)=[N:2][N:33]=[N:32]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 45136965HCID 45136965, compound

Product 1

HCID 178456076HCID 178456076, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A sealed tube was charged with 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid[(S)-1-(2-cyano-pyridin-4-yl)-propyl]-amide (75 mg, 0.19 mmol), sodium azide (37 mg, 0.58 mmol) and DMF (1 mL) and warmed at 120° C. After 16 hours, the reaction was diluted with a 4:1 mixture of acetonitrile in water, filtered and purified by reverse-phase chromatography. The desired fractions from the column were concentrated and dissolved in dichloromethane. The organic phase was washed with water, dried over sodium sulfate, filtered and concentrated to afford the title compound.

Workup

  1. filtrationfiltered
  2. custompurified by reverse-phase chromatography
  3. concentrationThe desired fractions from the column were concentrated
  4. dissolutiondissolved in dichloromethane
  5. washThe organic phase was washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ee136a8d538e42f79ec4c8c4f874f404
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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