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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
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인쇄 미리보기

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HRID 584846 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 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

생성물 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

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4007de42086140228fe9fbcf0beeda59
출처 데이터셋
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06927292B2

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