Ammonium formate → HCID 89552443, compound

HRID 1620127Notes

Reaction equation

HRID 1620127 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-1ef68d36665f4c4d8760a2cac97e90e8
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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