N-benzyl-1-butoxypyrido[4,3-c]-1,6-naphthyridin-6-amine → 6-(benzylamino)pyrido[4,3-c]-1,6-naphthyridin-1(2H)-one

HRID 2192972Notes

Reaction equation

HRID 2192972 reaction equation
[CH2:1]([NH:8][C:9]1[C:18]2[CH:19]=[CH:20][N:21]=[CH:22][C:17]=2[C:16]2[C:11](=[CH:12][CH:13]=[N:14][C:15]=2[O:23]CCCC)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Br>[CH2:1]([NH:8][C:9]1[C:18]2[CH:19]=[CH:20][N:21]=[CH:22][C:17]=2[C:16]2[C:15](=[O:23])[NH:14][CH:13]=[CH:12][C:11]=2[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 59375529N-benzyl-1-butoxypyrido[4,3-c]-1,6-naphthyridin-6-amine

Product 1

HCID 250949686-(benzylamino)pyrido[4,3-c]-1,6-naphthyridin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

N-benzyl-1-butoxypyrido[4,3-c]-1,6-naphthyridin-6-amine (90 mg, 0.251 mmol) was dissolved in hydrobromic acid (2.5 mL, 33% in acetic acid). The reaction mixture was left to stir overnight at room temperature. The reaction mixture was quenched with aqueous sodium hydrogen carbonate. The aqueous mixture was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative HPLC Reverse phase (C-18), eluting with Acetonitrile/Water+0.05% TFA, to afford 6-(benzylamino)pyrido[4,3-c]-1,6-naphthyridin-1(2H)-one as a red solid. 1H NMR (500 MHz, C2D6SO) δ 11.39 (d, 1H), 11.00 (s, 1H), 8.94 (t, 1H), 8.72 (d, 1H), 8.24 (d, 1H), 7.40 (t, 3H), 7.30 (t, 2H), 7.22 (t, 1H), 6.39 (d, 1H), 4.82 (d, 2H). LRMS (APCI) calc'd for (C18H15N4O) [M+H]+, 303.1; found 303.1.

Workup

  1. waitThe reaction mixture was left
  2. customThe reaction mixture was quenched with aqueous sodium hydrogen carbonate
  3. extractionThe aqueous mixture was extracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative HPLC Reverse phase (C-18)
  7. washeluting with Acetonitrile/Water+0.05% TFA

Sources & evidence

ORD record
ord-80f8a89f137149d190b4fc78f3e11956
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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