3-Chloro-1-methylbenzo[f][1,7]naphthyridin-5-amine → 1-Methylbenzo[f][1,7]naphthyridin-5-amine

HRID 340241Notes

Reaction equation

HRID 340241 reaction equation
Cl[C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[C:5]([NH2:17])[N:6]=[C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]3=2)[N:3]=1.[H][H]>C(OCC)(=O)C.CO.[Pd]>[CH3:12][C:10]1[C:9]2[C:4](=[C:5]([NH2:17])[N:6]=[C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]3=2)[N:3]=[CH:2][CH:11]=1

Participants

5

Reactant 2

HCID 866523483-Chloro-1-methylbenzo[f][1,7]naphthyridin-5-amineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 582137251-Methylbenzo[f][1,7]naphthyridin-5-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 3-chloro-1-methylbenzo[f][1,7]naphthyridin-5-amine (from step 3) in ethyl acetate/methanol (1:2, 0.03 M) was added 10% wt palladium on carbon (0.2 eq.). The reaction vessel was shaken on a hydrogen Pan apparatus under 50 psi of hydrogen overnight. The mixture was filtered through a pad of celite, washing with dichloromethane. The filtrate was concentrated en vacuo and purified by a COMBIFLASH® system (ISCO) using 0-80% ethyl acetate in hexane to give 1-methylbenzo[f][1,7]naphthyridin-5-amine as a white solid. 1H NMR (CDCl3): δ 8.63 (d, 1H), 8.44 (d, 1H), 7.71 (dd, 1H), 7.54 (m, 1H), 7.45 (d, 1H), 7.30 (m, 1H), 6.20 (bs, 2H), 3.01 (s, 3H). LRMS [M+H]=210.1.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. washwashing with dichloromethane
  3. concentrationThe filtrate was concentrated en vacuo
  4. custompurified by a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-e41fccc3622e4752822838ed2eeaa446
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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