Hydrochloric Acid → HCID 21073767, compound

HRID 1373563Notes

Reaction equation

HRID 1373563 reaction equation
C[O:2][C:3]1[CH2:12][C:11]2[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]4[N:33]=[C:32]5[C:27]([CH:28]=[CH:29][C:30](=[O:34])[NH:31]5)=[CH:26][CH:25]=4)[CH2:15][CH2:14]3)=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH:4]=1.Cl>C(O)C.O1CCCC1>[O:2]=[C:3]1[CH2:12][C:11]2[C:10]([N:13]3[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]4[N:33]=[C:32]5[C:27]([CH:28]=[CH:29][C:30](=[O:34])[NH:31]5)=[CH:26][CH:25]=4)[CH2:17][CH2:18]3)=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 210737637-{4-[4-(7-Methoxy-5,8-dihydro-naphthalen-1-yl)-piperazin-1-yl]-butoxy}-1H-[1,8]naphthyridin-2-one

Product 1

HCID 21073767HCID 21073767, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

7-{4-[4-(7-Methoxy-5,8-dihydro-naphthalen-1-yl)-piperazin-1-yl]-butoxy}-1H-[1,8]naphthyridin-2-one (360 mg, 0.78 mmol) was dissolved in a mixture of ethanol (6 mL) and tetrahydrofuran (2 mL). To this was added 10% hydrochloric acid (1.5 mL) and the mixture was stirred at room temperature for 15 minutes, then quenched with saturated sodium bicarbonate (10 mL). The mixture was extracted with ethyl acetate (20 mL) and the organic layer was washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered and evaporated. The crude solid was purified by column chromatography (6:94 triethylamine/ethyl acetate) to yield the title compound (263 mg, 75%) as a white foam. 1H NMR (400 MHz, CDCl3) δ 9.15 (s, 1H), 7.76 (d, 1H), 7.60 (d, 1H), 7.20 (t, 1H), 7.00–6.95 (m, 2H), 6.60 (d, 1H), 6.50 (d, 1H), 4.40 (t, 2H), 3.60 (s, 2H), 3.04 (t, 2H), 2.90–2.80 (m, 4H), 2.80–2.40 (m, 8H), 1.90–1.60 (m, 4H), MS ES+ 447.05 (M+H)+ (Exact mass: 446.23).

Workup

  1. customquenched with saturated sodium bicarbonate (10 mL)
  2. extractionThe mixture was extracted with ethyl acetate (20 mL)
  3. washthe organic layer was washed with brine (20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude solid was purified by column chromatography (6:94 triethylamine/ethyl acetate)

Sources & evidence

ORD record
ord-e8f53c8d865647d7a8dc0416666c7d53
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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