Ammonium formate → HCID 117643826, compound

HRID 2171281Notes

Reaction equation

HRID 2171281 reaction equation
C([O-])=O.[NH4+].[C:5]([C:7]1[CH:8]=[C:9]([F:49])[C:10]([NH:21][CH:22]2[CH2:27][CH2:26][N:25](C(OCC3C=CC=CC=3)=O)[CH2:24][CH:23]2[N:38]2[C:46](=[O:47])[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:39]2=[O:48])=[N:11][C:12]=1[NH:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([CH3:20])[CH:19]=1)#[N:6]>[Pd].C(OCC)(=O)C.CO>[O:48]=[C:39]1[C:40]2[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:46](=[O:47])[N:38]1[CH:23]1[CH:22]([NH:21][C:10]2[C:9]([F:49])=[CH:8][C:7]([C:5]#[N:6])=[C:12]([NH:13][C:14]3[CH:15]=[N:16][CH:17]=[C:18]([CH3:20])[CH:19]=3)[N:11]=2)[CH2:27][CH2:26][NH:25][CH2:24]1

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 117643277HCID 117643277, compound

Product 1

HCID 117643826HCID 117643826, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
70 °C

Procedure

Ammonium formate (6 mg) and 10% Pd/C (6 mg) were added to an ethyl acetate/MeOH (1 ml/1 ml) solution containing benzyl 4-((5-cyano-3-fluoro-6-((5-methylpyridin-3-yl)amino)pyridin-2-yl)amino)-3-(1,3-dioxoisoindolin-2-yl)piperidin-1-carboxylate (37 mg) obtained in the 1st step in a nitrogen atmosphere, followed by heating and stirring at 70° C. for 1 hour. Next, ammonium formate (30 mg) and 10% Pd/C (30 mg) were added to the solution, followed by heating and stirring at 70° C. for 1 hour. The reaction solution was cooled to room temperature and insoluble matter was removed by filtration through Celite. Filter cake was washed with ethyl acetate. The resulting filtrate was mixed with wash liquid. The obtained organic layers were washed with saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure. A white solid of 6-((3-(1,3-dioxoisoindolin-2-yl)piperidin-4-yl)amino)-5-fluoro-2-((5-methylpyridin-3-yl)amino)nicotinonitrile (15 mg) was thus obtained.

Workup

  1. customobtained in the 1st step in a nitrogen atmosphere
  2. temperatureby heating
  3. temperatureby heating
  4. stirringstirring at 70° C. for 1 hour
  5. temperatureThe reaction solution was cooled to room temperature
  6. custominsoluble matter was removed by filtration through Celite
  7. filtrationFilter cake
  8. washwas washed with ethyl acetate
  9. additionThe resulting filtrate was mixed
  10. washwith wash liquid
  11. washThe obtained organic layers were washed with saturated saline
  12. dry with materialdried over anhydrous sodium sulfate
  13. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-5f92f8e901c44d5080cd7aedef5ac329
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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