Methyl 5-amino-2-(4-methoxyphenethyl)benzo[f][1,7]naphthyridine-8-carboxylate → (5-Amino-2-(4-methoxyphenethyl)benzo[f][1,7]naphthyridin-8-yl)methanol

HRID 1259180Notes

Reaction equation

HRID 1259180 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][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[CH:7][C:6]=2[C:5]2[CH:22]=[CH:23][C:24]([C:26](OC)=[O:27])=[CH:25][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:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)=[CH:7][C:6]=2[C:5]2[CH:22]=[CH:23][C:24]([CH2:26][OH:27])=[CH:25][C:4]=2[N:3]=1

Participants

3

Reactant 1

HCID 58213534Methyl 5-amino-2-(4-methoxyphenethyl)benzo[f][1,7]naphthyridine-8-carboxylate

Product 1

HCID 58213730(5-Amino-2-(4-methoxyphenethyl)benzo[f][1,7]naphthyridin-8-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-amino-2-(4-methoxyphenethyl)benzo[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 minutes. 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 0-100% EtOAc/Hexanes to give (5-amino-2-(4-methoxyphenethyl)benzo[f][1,7]naphthyridin-8-yl)methanol as an off white solid (31%): 1H NMR (acetone-d6): δ 8.79 (d, 1H), 8.70 (d, 1H), 8.35 (d, 1H), 7.61 (d, 1H), 7.33 (dd, 1H), 7.13 (d, 2H), 6.83 (d, 2H), 6.62 (br s, 2H), 4.47 (s, 2H), 4.40 (br s, 1H), 3.75 (s, 3H), 3.22 (t, 2H), 3.06 (t, 2H). LRMS [M+H]=360.2.

Workup

  1. customThe reaction was 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-c54abee91a11403d9dfb51cbc573cc7c
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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