HCID 70921741, compound → N-(4-(4-Aminophenoxy)pyridin-2-yl)-2-methoxyacetamide

HRID 2069124Notes

Reaction equation

HRID 2069124 reaction equation
[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[CH:10]=[CH:9][N:8]=1)=[O:5].[H][H]>CO.C(Cl)Cl.CC(O)=O.[Pt]>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([O:13][C:11]2[CH:10]=[CH:9][N:8]=[C:7]([NH:6][C:4](=[O:5])[CH2:3][O:2][CH3:1])[CH:12]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 2

HCID 70921741HCID 70921741, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86660483N-(4-(4-Aminophenoxy)pyridin-2-yl)-2-methoxyacetamide

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23939PlatinumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 2-methoxy-N-(4-(4-nitrophenoxy)pyridin-2-yl)acetamide (730 mg, 2.41 mmol) in MeOH/DCM (1:1 v/v, 80 mL) containing AcOH (5 drops) was subjected to hydrogenation by passage through a Thales H-cube (1.0 mL min−1, RT, 70 mm 10% Pt/C Cat-Cart, full hydrogen mode) and was then evaporated in vacuo. The residue was partitioned between DCM (20 mL) and saturated aqueous NaHCO3 solution (10 mL). The organic layer was washed with brine (20 mL) and was dried (MgSO4) and evaporated in vacuo to afford the title compound, Intermediate H1, as a white solid (0.63 g, 91%); Rt 0.88 min (Method 2); m/z 274 (M+H)+ (ES+).

Workup

  1. customwas then evaporated in vacuo
  2. customThe residue was partitioned between DCM (20 mL) and saturated aqueous NaHCO3 solution (10 mL)
  3. washThe organic layer was washed with brine (20 mL)
  4. dry with materialwas dried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-06978fe4a3174253bc69875ca949a4d7
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

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