Methyl 5-amino-2-phenethylbenzo[f][1,7]naphthyridine-8-carboxylate → (5-Amino-2-phenethylbenzo[f][1,7]naphthyridin-8-yl)methanol

HRID 1259178Notes

Reaction equation

HRID 1259178 reaction equation
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:7][C:6]=2[C:5]2[CH:20]=[CH:21][C:22]([C:24](OC)=[O:25])=[CH:23][C:4]=2[N:3]=1>C1COCC1>[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:7][C:6]=2[C:5]2[CH:20]=[CH:21][C:22]([CH2:24][OH:25])=[CH:23][C:4]=2[N:3]=1

Participants

3

Reactant 1

HCID 66874950Methyl 5-amino-2-phenethylbenzo[f][1,7]naphthyridine-8-carboxylate

Product 1

HCID 58213577(5-Amino-2-phenethylbenzo[f][1,7]naphthyridin-8-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-amino-2-phenethylbenzo[f][1,7]naphthyridine-8-carboxylate (from the previous step) (1.0 eq.) in THF (0.03M) was added Super-H (10 eq.) at 0° C. The solution was allowed to warm to ambient temperature over 30 min The reaction was quenched by water until no bubbling. The layers were separated and aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4 and concentrated en vaccuo to obtain a crude residue. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-10% MeOH/DCM to give (5-amino-2-phenethylbenzo[f][1,7]naphthyridin-8-yl)methanol as an off white solid: 1H NMR (methanol-d4): δ 8.63 (dd, 1H), 8.56 (dd, 1H), 8.24 (d, 1H), 7.57 (d, 1H), 7.35 (dd, 1H), 7.27-7.15 (m, 5H), 4.75 (s, 2H), 3.20 (t, 2H), 3.06 (t, 2H). LRMS [M+H]=330.1.

Workup

  1. customwas quenched by water until no bubbling
  2. customThe layers were separated
  3. extractionaqueous layer was extracted with EtOAc
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated en vaccuo
  7. customto obtain a crude residue
  8. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-cf335070a7ea40278d1494f9cbe53978
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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