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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
ノート
印刷プレビュー

反応式

HRID 1373601 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 13387
N-methyl-2-pyrrolidone
溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-44e861d12db1469fbc7d540f700ea2ce
出典データセット
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07160888B2

反応ノート

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