Ammonium formate → HCID 178457833, compound

HRID 518766Notes

Reaction equation

HRID 518766 reaction equation
[CH:1]([NH:4][C:5]([C@H:7]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]2[CH:19]=[C:18]([CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:17]=[CH:16][C:15]=2[N+:27]([O-])=O)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>[Pd].CCO>[NH2:27][C:15]1[CH:16]=[CH:17][C:18]([CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)=[CH:19][C:14]=1[NH:13][C@@H:10]1[CH2:11][CH2:12][C@H:7]([C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH2:8][CH2:9]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 178457834HCID 178457834, compound

Product 1

HCID 178457833HCID 178457833, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a round bottom flask was added cis-N-isopropyl-4-(2-nitro-5-(piperidin-1-ylmethyl)phenylamino)cyclohexanecarboxamide (1.400 g, 3.48 mmol) under nitrogen. Palladium on carbon (0.370 g, 0.348 mmol) was added, followed by EtOH (28.3 mL) via syringe. To the reaction was added ammonium formate (2.193 g, 34.8 mmol), and the reaction mixture was stirred at RT overnight. The reaction mixture was filtered through Celite® brand filter aid, concentrated and diluted with 90:10:1 DCM:MeOH:NH4OH and water. The layers were separated, and the aqueous layer was washed once more. The organics were dried over sodium sulfate, filtered and concentrated to yield cis-4-(2-amino-5-(piperidin-1-ylmethyl)phenylamino)-N-isopropylcyclohexanecarboxamide (1.18 g, 3.17 mmol, 91% yield) as a dark red solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite® brand
  2. filtrationfilter aid
  3. concentrationconcentrated
  4. additiondiluted with 90:10:1 DCM
  5. customThe layers were separated
  6. washthe aqueous layer was washed once more
  7. dry with materialThe organics were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0354c5921517497bbbbe5b0c43cb34bc
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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