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4-(4-Naphthalen-1-yl-piperazin-1-yl)-butan-1-ol → 4,4-Dimethyl-7-[4-(4-naphthalen-1-yl-piperazin-1-yl)-butoxy]-3,4-dihydro-1H-[1,8]naphthyridin-2-one

HRID 1373601
Notes
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Reaction equation

HRID 1373601 reaction equation
F[C:2]1[N:11]=[C:10]2[C:5]([C:6]([CH3:14])([CH3:13])[CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[C:15]1([N:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][CH2:34][OH:35])[CH2:27][CH2:26]2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.CC(C)([O-])C.[Na+]>CN1C(=O)CCC1>[CH3:13][C:6]1([CH3:14])[C:5]2[C:10](=[N:11][C:2]([O:35][CH2:34][CH2:33][CH2:32][CH2:31][N:28]3[CH2:29][CH2:30][N:25]([C:15]4[C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[CH:18]=[CH:17][CH:16]=4)[CH2:26][CH2:27]3)=[CH:3][CH:4]=2)[NH:9][C:8](=[O:12])[CH2:7]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 210733524-(4-Naphthalen-1-yl-piperazin-1-yl)-butan-1-olHCID 210739217-Fluoro-4,4-dimethyl-1,2,3,4-tetrahydro-1,8-naphthyridin-2-oneHCID 23676156Sodium t-butoxide

Product 1

HCID 115035074,4-Dimethyl-7-[4-(4-naphthalen-1-yl-piperazin-1-yl)-butoxy]-3,4-dihydro-1H-[1,8]naphthyridin-2-oneYield 48%

Reagents, catalysts & solvents 1

HCID 13387
N-methyl-2-pyrrolidone
Solvent

Conditions

Temperature
70 °C

Procedure

7-Fluoro-4,4-dimethyl-3,4-dihydro-1H-[1,8]naphthyridin-2-one (247 mg, 1.272 mmol), 4-(4-naphthalen-1-yl-piperazin-1-yl)-butan-1-ol (365 mg, 1.285 mmol) and sodium t-butoxide (367 mg, 3.82 mmol) were combined in a dried flask 3 necked flask under N2. NMP was added and the solution was heated in an oil bath to 70° C. for 4 hours. The reaction was cooled to room temperature and poured into ice water. The solid that was collected was slurried in CH2Cl2 and ethyl acetate and purified by liquid chromatography (MPLC, gradient of 100% CH2Cl2 to 100% ethyl acetate) to give the title compound as a foam (280 mg, 0.610 mmol, 48%). MS: APCI: M+1: 459.2 (Exact Mass: 458.27).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customThe solid that was collected
  3. customethyl acetate and purified by liquid chromatography (MPLC, gradient of 100% CH2Cl2 to 100% ethyl acetate)

Sources & evidence

ORD record
ord-44e861d12db1469fbc7d540f700ea2ce
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07160888B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes