Sodium triacetoxyborohydride → 7-{4-[4-(5-Chloro-2-isopropoxy-phenyl)-piperazin-1-yl]-butoxy}-3,4-dihydro-1H-[1,8]naphthyridin-2-one

HRID 1373533

反応式

HRID 1373533 の反応式
[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[C:8]([O:12][CH2:13][CH2:14][CH2:15][CH:16]=O)[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([O:31][CH:32]([CH3:34])[CH3:33])=[C:23]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C.CCOC(C)=O>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([O:31][CH:32]([CH3:34])[CH3:33])=[C:23]([N:25]2[CH2:26][CH2:27][N:28]([CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:8]3[N:9]=[C:10]4[C:5]([CH2:4][CH2:3][C:2](=[O:1])[NH:11]4)=[CH:6][CH:7]=3)[CH2:29][CH2:30]2)[CH:24]=1

参加物

6

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 210731661-(5-Chloro-2-isopropoxy-phenyl)-piperazineHCID 210733774-((7-Oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)oxy)butanal

生成物 1

HCID 210737117-{4-[4-(5-Chloro-2-isopropoxy-phenyl)-piperazin-1-yl]-butoxy}-3,4-dihydro-1H-[1,8]naphthyridin-2-one収率 45.4%

試薬・触媒・溶媒 2

HCID 63651,1-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of 4-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde (0.241 g, 1.02 mmol, 1 eq) and 1-(5-chloro-2-isopropoxy-phenyl)-piperazine (0.382 g, 1.13 mmol, 1.1 eq) in dichloroethane (5 mL) was added NaBH(OAc)3 (0.583 g, 2.75 mmol, 2.67 eq). The slurry was allowed to stir overnight at room temperature (18 h). Analysis by HPLC showed reaction mostly complete. The mixture was diluted with EtOAc and quenched with saturated NaHCO3. The organic phase was then washed with brine, dried over Na2SO4, filtered and evaporated in vacuo. Purification by silica gel chromatography (100% EtOAc) followed by formation of the HCl salt using 1N HCl in ether provided the title compound (0.219 g, 25%). MS: APCI: M+1: 473.2 (Exact Mass: 472.22).

後処理

  1. customreaction mostly complete
  2. customquenched with saturated NaHCO3
  3. washThe organic phase was then washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customPurification by silica gel chromatography (100% EtOAc)

出典と根拠

ORDレコード
ord-dd37439ed99643c7a02d08a9e358a307
出典データセット
uspto-grants-2007_01
特許番号
US07160888B2

関連ノート

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