Ammonium formate → HCID 89552443, compound

HRID 340520Notes

Reaction equation

HRID 340520 reaction equation
C([O-])=O.[NH4+].[C:5]([O:9][C:10](=[O:44])[NH:11][C@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]1[NH:18][C:19]1[C:24]([F:25])=[CH:23][C:22]([C:26]#[N:27])=[C:21]([NH:28][C:29]2[CH:30]=[N:31][CH:32]=[C:33]([C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([N+:41]([O-])=O)[CH:36]=3)[CH:34]=2)[N:20]=1)([CH3:8])([CH3:7])[CH3:6]>[Pd].CO>[C:5]([O:9][C:10](=[O:44])[NH:11][C@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]1[NH:18][C:19]1[C:24]([F:25])=[CH:23][C:22]([C:26]#[N:27])=[C:21]([NH:28][C:29]2[CH:30]=[N:31][CH:32]=[C:33]([C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([NH2:41])[CH:36]=3)[CH:34]=2)[N:20]=1)([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 89552441HCID 89552441, compound

Product 1

HCID 89552443HCID 89552443, compoundYield 109.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ammonium formate (0.2 g) and 10% Pd/C (0.2 g) were added to a methanol (10 ml) solution containing tert-butyl((1S,2R)-2-((5-cyano-3-fluoro-6-((5-(3-nitrophenyl)pyridin-3-yl)amino)pyridin-2-yl)amino)cyclohexyl)carbamate (87 mg), followed by reflux with heating for 30 minutes. The reaction mixture was cooled to room temperature and filtered with Celite, the solvent was distilled away under reduced pressure, and a yellow solid of tert-butyl((1S,2R)-2-((6-((5-(3-aminophenyl)pyridin-3-yl)amino)-5-cyano-3-fluoropyridin-2-yl)amino)cyclohexyl)carbamate (90 mg) was thus obtained.

Workup

  1. temperatureby reflux
  2. temperaturewith heating for 30 minutes
  3. filtrationfiltered with Celite
  4. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-24024b62e48e46caac66bf62633e2127
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

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