Methanol → HCID 67455138, compound

HRID 639648Notes

Reaction equation

HRID 639648 reaction equation
[CH2:1]([NH:8][C:9]1[C:14]([N+:15]([O-])=O)=[C:13]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:12]=[C:11]([C:26]2[O:27][CH:28]=[CH:29][N:30]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO>C1COCC1.[Ni]>[CH2:1]([NH:8][C:9]1[C:14]([NH2:15])=[C:13]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:12]=[C:11]([C:26]2[O:27][CH:28]=[CH:29][N:30]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 67455402HCID 67455402, compound

Product 1

HCID 67455138HCID 67455138, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

N*2*,N*4*-Dibenzyl-3-nitro-6-oxazol-2-yl-pyridine-2,4-diamine (1.02 g, 2.54 mmol) was dissolved in THF (60 ml) then MeOH (60 ml) was added. The solution was hydrogenated over Raney nickel (210 mg, 0.25 mmol) under a hydrogen atmosphere (80 psi) for 1 hour. The reaction mixture was filtered through a Celite pad then evaporated to yield the title compound as a brown gum (944 mg, 100%). Taken on without further purification due to stability concerns.

Workup

  1. customfor 1 hour
  2. filtrationThe reaction mixture was filtered through a Celite pad
  3. customthen evaporated

Sources & evidence

ORD record
ord-2547ffebfa1945c889172e4eb3c56743
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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