HCID 178501201, compound → HCID 178501200, compound

HRID 518595Notes

Reaction equation

HRID 518595 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[NH:10][C@@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]([O:19][CH3:20])=[O:18])[CH2:13][CH2:12]1)([O-])=O>[Pd].CCO>[NH2:1][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[NH:10][C@@H:11]1[CH2:12][CH2:13][C@H:14]([C:17]([O:19][CH3:20])=[O:18])[CH2:15][CH2:16]1

Participants

4

Reactant 1

HCID 178501201HCID 178501201, compound

Product 1

HCID 178501200HCID 178501200, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A round bottom flask under nitrogen atmosphere was charged with cis-methyl 4-(3-nitropyridin-4-ylamino)cyclohexanecarboxylate (1.1 g, 3.94 mmol) and Pd/C (10% wt) (0.419 g, 0.394 mmol). EtOH (16 mL) was added, and the reaction mixture was purged with nitrogen 3 times. A H2-filled balloon was attached to the top of the flask, and the mixture stirred at RT for 2 hours. The reaction mixture was diluted with EtOH and filtered through Celite® brand filter aid. The pad was washed with DCM (50 mL), EtOH (50 mL), and MeOH (50 mL). The filtrate was concentrated to dryness to afford cis-methyl 4-(3-aminopyridin-4-ylamino)cyclohexanecarboxylate as a purple oil. (0.9 g, 92.0% yield). MS m/z=250.2 [M+H]. Calc'd for C13H19N3O2: 249.2.

Workup

  1. customthe reaction mixture was purged with nitrogen 3 times
  2. additionA H2-filled balloon
  3. additionThe reaction mixture was diluted with EtOH
  4. filtrationfiltered through Celite® brand
  5. filtrationfilter aid
  6. washThe pad was washed with DCM (50 mL), EtOH (50 mL), and MeOH (50 mL)
  7. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-d40edc173bb64fcc96c4e8d329ea9dd7
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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