HCID 58213602, compound → HCID 58213705, compound

HRID 340234Notes

Reaction equation

HRID 340234 reaction equation
[CH3:1][O:2][CH2:3]/[CH:4]=[CH:5]/[C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[C:13]1[CH:16]=[CH:17][CH:18]=[CH:19][C:12]1=[N:11][C:10]=2[NH2:20].[H][H]>C(OCC)(=O)C.CO.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[C:13]1[CH:16]=[CH:17][CH:18]=[CH:19][C:12]1=[N:11][C:10]=2[NH2:20]

Participants

5

Reactant 2

HCID 58213602HCID 58213602, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58213705HCID 58213705, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of (E)-2-(3-methoxyprop-1-enyl)benzo[f][1,7]naphthyridin-5-amine (Example 34) in ethyl acetate/methanol (1:4, 0.05 M) was added 10% wt palladium on carbon (0.2 eq.). Hydrogen gas was introduced via a balloon, and the reaction was stirred for 3 hours. The mixture was filtered through a pad of celite, washing with dichloromethane. The filtrate was concentrated en vacuo and the crude product was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-80% ethyl acetate in hexane to give 2-(3-methoxypropyl)benzo[f][1,7]naphthyridin-5-amine as a white solid. 1H NMR (CDCl3): δ 8.64 (d, 1H), 8.46 (d, 1H), 8.19 (d, 1H), 7.66 (d, 1H), 7.53 (m, 1H), 7.31 (m, 1H), 6.56 (bs, 2H), 3.37 (t, 2H), 3.31 (s, 3H), 2.91 (t, 2H), 1.93-2.00 (m, 2H). LRMS [M+H]=268.1.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. washwashing with dichloromethane
  3. concentrationThe filtrate was concentrated en vacuo
  4. customthe crude product was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-5ef6dec50c1c4bfa8baed0534d75ab8c
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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