Ammonia → HCID 178513760, compound

HRID 456635Notes

Reaction equation

HRID 456635 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]=2)[NH:8][CH:7]=1)=O)C.F[P-](F)(F)(F)(F)F.FC(N(C)C)=[N+:29](C)C.C(N(CC)C(C)C)(C)C.N>C(#N)C>[NH:13]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:19]2[C:11]([C:9]2[NH:8][CH:7]=[C:6]([C:4]([NH2:29])=[O:3])[CH:10]=2)=[N:12]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 2774761Tetramethylfluoroformamidinium hexafluorophosphateHCID 178469891HCID 178469891, compound

Product 1

HCID 178513760HCID 178513760, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 5-(1H-pyrazolo[3,4-b]pyridin-3-yl)-1H-pyrrole-3-carboxylic acid (80 mg, 0.35 mmol) (from Example 11) and fluoro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (92.7 mg, 0.35 mmol) (Aldrich, Milwaukee, Wis.) in acetonitrile (6 mL) at 0° C. was added N,N-diisopropylethylamine (DIPEA) (54.28 mg, 0.42 mmol). The mixture was allowed to warm up to room temperature and stirred for one hour. The mixture was then cooled in an ice-bath and charged with ammonia gas. After stirring at room temperature for overnight, the reaction was concentrated, diluted with water and extracted with DCM. The organic layer was concentrated and triturated with DCM to give the titled compound.

Workup

  1. temperatureThe mixture was then cooled in an ice-bath
  2. stirringAfter stirring at room temperature for overnight
  3. concentrationthe reaction was concentrated
  4. additiondiluted with water
  5. extractionextracted with DCM
  6. concentrationThe organic layer was concentrated
  7. customtriturated with DCM

Sources & evidence

ORD record
ord-be393f4711e74eda982a2ee4de43452d
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

Loading…