Triethylamine → 7-{4-[4-(2,3-Dichloro-phenyl)-piperazin-1-yl]-butoxy}-5-methyl-3,4-dihydro-1H-[1,8]naphthyridin-2-one

HRID 1373610

反応式

HRID 1373610 の反応式
Cl.[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.CCN(CC)CC.[CH3:23][C:24]1[C:33]2[CH2:32][CH2:31][C:30](=[O:34])[NH:29][C:28]=2[N:27]=[C:26]([O:35][CH2:36][CH2:37][CH2:38][CH:39]=O)[CH:25]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C.C(Cl)Cl>[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:39][CH2:38][CH2:37][CH2:36][O:35][C:26]2[N:27]=[C:28]3[C:33]([CH2:32][CH2:31][C:30](=[O:34])[NH:29]3)=[C:24]([CH3:23])[CH:25]=2)[CH2:12][CH2:11]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 116303721-(2,3-Dichlorophenyl)piperazine hydrochlorideHCID 210733504-(4-Methyl-7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde

生成物 1

HCID 115617337-{4-[4-(2,3-Dichloro-phenyl)-piperazin-1-yl]-butoxy}-5-methyl-3,4-dihydro-1H-[1,8]naphthyridin-2-one収率 70.5%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 63651,1-Dichloroethane溶媒2 回

実験手順

To a suspension of 1-(2,3-dichloro-phenyl)-piperazine hydrochloride (0.93 g, 3.48 mmol) in dichloroethane (10 mL) was added Et3N (0.96 mL, 6.92 mmol). The mixture was stirred for 15 min and a suspension of 4-(4-methyl-7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde (0.86 g, 3.46 mmol) in dichloroethane (5 mL) was added. After 20 min at RT, NaBH(OAc)3 (1.03 g, 4.85 mmol) was added and the reaction was stirred at room temperature for 4 h. The reaction mixture was poured into CH2Cl2 and washed with H2O, 1N citric acid, saturated NaHCO3 and brine, dried over Na2SO4 and concentrated to an oil. Et2O was added and the organics were decanted from an insoluble gum. The filtrate yielded a crystalline solid, which was collected by filtration and dried. Purification by liquid chromatography (gradient elution, 100% CHCl3 to 2% MeOH/CHCl3, Biotage 40m column) provided the title compound as a white solid (1.12 g, 2.44 mmol, 70%). MS: APCI: M+1: 463.1 (Exact Mass: 462.16).

後処理

  1. additionwas added
  2. waitAfter 20 min at RT
  3. stirringthe reaction was stirred at room temperature for 4 h
  4. washwashed with H2O, 1N citric acid, saturated NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to an oil
  7. additionEt2O was added
  8. customthe organics were decanted from an insoluble gum
  9. customThe filtrate yielded a crystalline solid, which
  10. filtrationwas collected by filtration
  11. customdried
  12. customPurification
  13. washby liquid chromatography (gradient elution, 100% CHCl3 to 2% MeOH/CHCl3, Biotage 40m column)

出典と根拠

ORDレコード
ord-f99058e8660f4b7ab497df16805c2368
出典データセット
uspto-grants-2007_01
特許番号
US07160888B2

関連ノート

読み込み中…