Stannous Chloride → HCID 178457830, compound

HRID 518692Notes

Reaction equation

HRID 518692 reaction equation
[Cl:1][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[Sn]Cl>CO>[NH2:21][C:5]1[C:6]([NH:8][C@@H:9]2[CH2:10][CH2:11][C@H:12]([C:15]([NH:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]2)=[CH:7][C:2]([Cl:1])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 178457831HCID 178457831, compound

Product 1

HCID 178457830HCID 178457830, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of cis-4-(2-chloro-5-nitropyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide (400 mg, 1.174 mmol) in MeOH (2.3 mL) was added SnCl2 (890 mg, 4.69 mmol), and the mixture was stirred at reflux for 2 hours. The mixture was evaporated and partitioned between 10% IPA/DCM and saturated NaHCO3. The solids were removed by filtration through Celite® brand filter aid, and the organic layer was washed with water, saturated NaHCO3, dried over Na2SO4 and filtered. The mixture was purified via flash chromatography using a linear gradient of 0% to 10% of 1% NH4OH in MeOH in DCM. The title compound was collected as a white solid (160 mg, 44% yield).

Workup

  1. temperatureat reflux for 2 hours
  2. customThe mixture was evaporated
  3. custompartitioned between 10% IPA/DCM and saturated NaHCO3
  4. customThe solids were removed by filtration through Celite® brand
  5. filtrationfilter aid
  6. washthe organic layer was washed with water, saturated NaHCO3
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customThe mixture was purified via flash chromatography

Sources & evidence

ORD record
ord-e674d5bca26844ff9ba52c7acec3f4db
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

Loading…