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 340312Notes

Reaction equation

HRID 340312 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 vacuo 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 vacuo
  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-2803ace231504339b728322a00a07ee2
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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