Hydrochloric Acid → 4-(3-aminopyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide

HRID 518684Notes

Reaction equation

HRID 518684 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([NH:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[C:5]([N+:21]([O-])=O)=[CH:4][N:3]=1.Cl.C([O-])=O.[NH4+]>CCO.[Pd]>[NH2:21][C:5]1[CH:4]=[N:3][CH:2]=[CH:7][C:6]=1[NH:8][CH:9]1[CH2:10][CH2:11][CH:12]([C:15]([NH:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2723923Ammonium formateHCID 178457831HCID 178457831, compound

Product 1

HCID 667286674-(3-aminopyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of cis-4-(2-chloro-5-nitropyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide (100 mg, 0.293 mmol) and conc. HCl (0.072 mL, 0.880 mmol) in EtOH (3.0 mL) under nitrogen was added Pd/C (10% wt) (156 mg, 0.147 mmol) and ammonium formate (185 mg, 2.93 mmol), and the mixture was stirred at RT for 30 minutes. The mixture was filtered through a pad of Celite® brand filter aid and evaporated. The residue was diluted with 10% IPA in DCM, and washed with 1 N NaOH and then with saturated aqueous NaHCO3. The organic layer was dried over Na2SO4, filtered and the solvent was removed to afford 4-(3-aminopyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide as an off-white solid.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite® brand
  2. filtrationfilter aid
  3. customevaporated
  4. additionThe residue was diluted with 10% IPA in DCM
  5. washwashed with 1 N NaOH
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-5a0cd916b7284d8ebc708cdcc3ee64df
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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