7-Chloro-1-methyl-1,8-naphthyridin-2(1H)-one → 1-Methyl-7-[4-(4-naphthalen-1-yl-piperazin-1-yl)-butoxy]-1H-[1,8]naphthyridin-2-one

HRID 1373567Notes

Reaction equation

HRID 1373567 reaction equation
[C:1]1([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl[C:23]1[N:32]=[C:31]2[C:26]([CH:27]=[CH:28][C:29](=[O:34])[N:30]2[CH3:33])=[CH:25][CH:24]=1>C1COCC1>[CH3:33][N:30]1[C:31]2[C:26](=[CH:25][CH:24]=[C:23]([O:21][CH2:20][CH2:19][CH2:18][CH2:17][N:14]3[CH2:13][CH2:12][N:11]([C:1]4[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH:4]=[CH:3][CH:2]=4)[CH2:16][CH2:15]3)[N:32]=2)[CH:27]=[CH:28][C:29]1=[O:34]

Participants

4

Reactant 2

HCID 124551927-Chloro-1-methyl-1,8-naphthyridin-2(1H)-oneHCID 210733524-(4-Naphthalen-1-yl-piperazin-1-yl)-butan-1-ol

Product 1

HCID 210731981-Methyl-7-[4-(4-naphthalen-1-yl-piperazin-1-yl)-butoxy]-1H-[1,8]naphthyridin-2-oneYield 77.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(4-naphthalen-1-yl-piperazin-1-yl)-butan-1-ol (422 mg, 1.48 mmol) in THF (5 mL) cooled to 0° C. was added 7-chloro-1-methyl-1H-[1,8]naphthyridin-2-one (303 mg, 1.56 mmol) as a solution in THF (9 mL) via cannula. The reaction was stirred for about 2 h at 0° C. The reaction was quenched with saturated NH4Cl and the mixture was extracted with EtOAc. The organic layer was washed with saturated NaHCO3 and brine, dried over Na2SO4 and concentrated. Purification by LC (4% MeOH/CH2Cl2) gave the title compound as a white foam (507 mg, 1.15 mmol, 77%). A portion of the title compound (243 mg, 0.549 mmol) was dissolved in Et2O and 1 N HCl in Et2O (0.55 mL) was added. The resulting white precipitate was collected by filtration, washed with Et2O and dried to give a white solid (248 mg). MS: APCI: M+1: 443.3 (Exact Mass: 442.24).

Workup

  1. customThe reaction was quenched with saturated NH4Cl
  2. extractionthe mixture was extracted with EtOAc
  3. washThe organic layer was washed with saturated NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by LC (4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-c6a2065e419f42fdb8f0a8840cd93f57
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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