HCID 178493218, compound → HCID 178493217, compound

HRID 518686Notes

Reaction equation

HRID 518686 reaction equation
[CH:1]([NH:4][C:5]([C@H:7]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]2[C:19]([N+:20]([O-])=O)=[CH:18][N:17]=[C:16]([O:23][CH3:24])[CH:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]>CC(O)=O.CO.C(Cl)Cl.[Fe]>[NH2:20][C:19]1[C:14]([NH:13][C@@H:10]2[CH2:9][CH2:8][C@H:7]([C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH2:12][CH2:11]2)=[CH:15][C:16]([O:23][CH3:24])=[N:17][CH:18]=1

Participants

5

Reactant 1

HCID 178493218HCID 178493218, compound

Product 1

HCID 178493217HCID 178493217, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
100 °C

Procedure

To solution of cis-N-isopropyl-4-(2-methoxy-5-nitropyridin-4-ylamino)cyclohexanecarboxamide (264 mg, 0.785 mmol) in AcOH (1.5 μmL) was added iron powder (219 mg, 3.92 mmol), and the mixture was heated to 100° C. for 5 minutes. The mixture was allowed to cool to RT, was diluted with 10% MeOH/DCM, and was filtered through a pad of Celite® brand filter aid and concentrated. The mixture was purified via flash chromatography using a linear gradient of 0% to 10% of 1% NH4OH in MeOH in DCM. Cis-4-(5-amino-2-methoxypyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide was isolated as a red film (211 mg).

Workup

  1. temperatureto cool to RT
  2. filtrationwas filtered through a pad of Celite® brand
  3. filtrationfilter aid
  4. concentrationconcentrated
  5. customThe mixture was purified via flash chromatography

Sources & evidence

ORD record
ord-21edec77d3da449983600a9e5e23a7d9
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

Loading…