HCID 21073764, compound → HCID 21073768, compound

HRID 1373543Notes

Reaction equation

HRID 1373543 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]([CH2:28][CH2:29][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>C(O)C.Cl>[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]([CH2:28][CH2:29][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

4

Reactant 1

HCID 21073764HCID 21073764, compound

Product 1

HCID 21073768HCID 21073768, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

7-{4-[4-(7-Methoxy-5,8-dihydro-naphthalen-1-yl)-piperazin-1-yl]-butoxy}-3,4-dihydro-1H-[1,8]naphthyridin-2-one (325 mg, 0.704 mmol) was dissolved in ethanol (5 mL) and 10% HCl (1 mL). The mixture was stirred at room temperature for 2 hours then quenched with saturated sodium bicarbonate (10 mL) and extracted with ethyl acetate (20 mL). 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 (2:98 methanol/ethyl acetate) to yield the title compound (180 mg, 57%) as a white foam. 1H NMR (400 MHz, CDCl3) δ 7.60 (s, 1H), 7.38 (d, 1H), 7.20 (t, 1H), 7.02–6.96 (m, 2H), 6.36 (d, 1H), 4.20 (t, 2H), 3.60 (s, 2H), 2.06 (t, 2H), 3.00–2.80 (m, 6H), 2.80–2.40 (m, 10H), 1.80–1.60 (4H); MS ES+ 449.06 (M+H)+ (Exact mass: 448.25).

Workup

  1. customthen quenched with saturated sodium bicarbonate (10 mL)
  2. extractionextracted 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 (2:98 methanol/ethyl acetate)

Sources & evidence

ORD record
ord-6ac7cbb5e1144b1480bde5917a4fbfdb
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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