HCID 90032751, compound → HCID 118223452, compound

HRID 2200100Notes

Reaction equation

HRID 2200100 reaction equation
[CH3:1][C:2]1[C:3]([O:11][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]([CH:21]3[CH2:23][CH2:22]3)=[O:20])[CH:13]=2)=[N:4][CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1>CO.C(Cl)Cl>[NH2:8][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([O:11][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]([CH:21]3[CH2:22][CH2:23]3)=[O:20])[CH:13]=2)=[N:4][CH:5]=1

Participants

4

Reactant 1

HCID 90032751HCID 90032751, compound

Product 1

HCID 118223452HCID 118223452, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve N-[4-[(3-methyl-5-nitro-2-pyridyl)oxy]-2-pyridyl]cyclopropanecarboxamide (269 mg, 0.83 mmol) in MeOH (5 mL) and DCM (5 mL). Add Pd/C (10%, 104 mg), flush with H2. Stir the reaction under H2 at room temperature for 2 hrs. After the reaction, flush with N2, filter the reaction mixture; concentrate the filtrate under reduced pressure to give the crude product. Purification by chromatography (silica gel, EtOAc:PE=1:1) affords the title compound (70 mg, 30%). MS: (M+1): 285.

Workup

  1. customAdd Pd/C (10%, 104 mg), flush with H2
  2. customthe reaction under H2 at room temperature for 2 hrs
  3. customAfter the reaction
  4. customflush with N2
  5. filtrationfilter the reaction mixture
  6. concentrationconcentrate the filtrate under reduced pressure
  7. customto give the crude product
  8. customPurification by chromatography (silica gel, EtOAc:PE=1:1)

Sources & evidence

ORD record
ord-19315eb3b0564c57ab179d24a684b2ab
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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