HCID 58213749, compound → HCID 58213746, compound

HRID 1479524Notes

Reaction equation

HRID 1479524 reaction equation
[CH2:1]=[C:2]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([CH:13]=1)=[C:11]1[CH:14]=[CH:15][CH:16]=[CH:17][C:10]1=[N:9][C:8]=2[NH2:18])[CH3:3].[H][H]>C(OCC)(=O)C.CO.[Pd]>[CH:2]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([CH:13]=1)=[C:11]1[CH:14]=[CH:15][CH:16]=[CH:17][C:10]1=[N:9][C:8]=2[NH2:18])([CH3:3])[CH3:1]

Participants

5

Reactant 2

HCID 58213749HCID 58213749, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58213746HCID 58213746, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 2-(prop-1-en-2-yl)benzo[f][1,7]naphthyridin-5-amine (Example 36) 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-isopropylbenzo[f][1,7]naphthyridin-5-amine as a yellow solid. 1H NMR (CDCl3): δ 8.69 (d, 1H), 8.49 (d, 1H), 8.25 (dd, 1H), 7.65 (dd, 1H), 7.53 (m, 1H), 7.31 (m, 1H), 6.02 (bs, 2H), 3.15 (septet, 1H), 1.37 (d, 6H). LRMS [M+H]=238.2.

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-b6198f4f843d4ba3a5b1d45a3d430966
Source dataset
uspto-grants-2016_08
Patent number
US09408907B2

Reaction notes

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