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Acetyl chloride → (8R,9R)-8,10-Diacetyl-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

HRID 584846
ノート
印刷プレビュー

反応式

HRID 584846 の反応式
[CH3:1][C:2]1[N:3]=[C:4]2[C:13]3[NH:12][C@H:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C@@H:10](O)[C:9](=[O:21])[C:8]=3[CH:7]=[CH:6][N:5]2[C:22]=1[CH3:23].[C:24](Cl)(=[O:26])[CH3:25].C(N([CH2:33][CH3:34])CC)C.C(=O)([O-])[OH:36].[Na+]>ClCCl.O>[C:24]([C@@H:10]1[C:9](=[O:21])[C:8]2[CH:7]=[CH:6][N:5]3[C:22]([CH3:23])=[C:2]([CH3:1])[N:3]=[C:4]3[C:13]=2[N:12]([C:33](=[O:36])[CH3:34])[C@H:11]1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)(=[O:26])[CH3:25]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 59943673(8R,9R)-2,3-dimethyl-8-hydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

生成物 1

HCID 69551346(8R,9R)-8,10-Diacetyl-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6344Dichloromethane溶媒

実験手順

50 g of (8R,9R)-2,3-dimethyl-8-hydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one (WO 00/17200, example B1) are dissolved under nitrogen and with exclusion of moisture in 450 ml of dichloromethane. Half of the amount of acetyl chloride (46.6 ml in total) is firstly added dropwise at room temperature. Half the amount of triethylamine (45 ml in total) is then added dropwise with ice cooling in the course of 30 min. After stirring at room temperature for 1 h, the procedure is repeated as described with the second half of the reagents indicated. The mixture is then hydrolyzed using saturated sodium hydrogencarbonate solution and water. The organic phase is separated off and the aqueous phase is extracted with dichloromethane. The combined organic phases are dried over magnesium sulfate and evaporated. The yellow-brown residue is coevaporated a further two times with toluene. 64 g of the title compound are isolated as a brown oil, which is used in the next stage without further purification.

後処理

  1. customThe organic phase is separated off
  2. extractionthe aqueous phase is extracted with dichloromethane
  3. dry with materialThe combined organic phases are dried over magnesium sulfate
  4. customevaporated

出典と根拠

ORDレコード
ord-4007de42086140228fe9fbcf0beeda59
出典データセット
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06927292B2

反応ノート

読み込み中…

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