7-methoxy-N-methyl-N-(4-nitrophenyl)-1,5-naphthyridin-4-amine → HCID 67317033, compound

HRID 503559Notes

Reaction equation

HRID 503559 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([N:13]([CH3:23])[C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[N:5][CH:4]=1.[H][H]>CO.[Pd].CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([N:13]([CH3:23])[C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[N:5][CH:4]=1

Participants

6

Reactant 2

HCID 673172097-methoxy-N-methyl-N-(4-nitrophenyl)-1,5-naphthyridin-4-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 67317033HCID 67317033, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 7-methoxy-N-methyl-N-(4-nitrophenyl)-1,5-naphthyridin-4-amine (0.233 g, 0.751 mmol) in MeOH (10 mL) at RT was added a suspension of 10% palladium on carbon (0.0799 g, 0.751 mmol) in EtOAc (10 mL). The mixture was exposed to an atmosphere of hydrogen (balloon). After 4 h, the mixture was filtered over celite and concentrated in vacuo. The crude yellow foam, N1-(7-methoxy-1,5-naphthyridin-4-yl)-NI-methylbenzene-1,4-diamine, was advanced without further purification. [email protected] min.

Workup

  1. additionwas added
  2. filtrationthe mixture was filtered over celite and
  3. concentrationconcentrated in vacuo
  4. customThe crude yellow foam, N1-(7-methoxy-1,5-naphthyridin-4-yl)-NI-methylbenzene-1,4-diamine, was advanced without further purification
  5. custom[email protected] min.

Sources & evidence

ORD record
ord-4453179abb7446a0bba00113caf053a0
Source dataset
uspto-grants-2010_08
Patent number
US07776857B2

Reaction notes

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