HCID 89738582, compound → HCID 131734539, compound

HRID 592057Notes

Reaction equation

HRID 592057 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([NH:11][C@@H:12]2[C@@H:17]3[O:18][C@@H:14]([CH2:15][CH2:16]3)[C@@H:13]2[C:19]([NH2:21])=[O:20])[C:5]([Cl:22])=[CH:4][N:3]=1>[Ni]>[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([NH:11][CH:12]2[CH:17]3[O:18][CH:14]([CH2:15][CH2:16]3)[CH:13]2[C:19]([NH2:21])=[O:20])[C:5]([Cl:22])=[CH:4][N:3]=1

Participants

3

Reactant 1

HCID 89738582HCID 89738582, compound

Product 1

HCID 131734539HCID 131734539, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

To a suspension of Raney Nickel (70 mg) in MeOH (25 ml) (1S,2R,3S,4R)-3-(2-amino-5-chloro-3-nitropyridin-4-ylamino)-7-oxabicyclo[2.2.1]heptane-2-carboxamide (16) (150 mg, 0.458 mmol) was added and the reaction mixture was hydrogenated for 2 h at rt. The reaction mixture was filtered through a bed of celite and the bed was washed well with MeOH. The filtrate was concentrated to afford the product (131 mg, 96%) as a white solid. LCMS (254 nm): [M+H]+ 298.10 (99.9%)

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered through a bed of celite
  3. washthe bed was washed well with MeOH
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0b1a35dce21746b0a2f4e1bd5cc944e2
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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