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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
Notes
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Reaction equation

HRID 584846 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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

Product 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

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4007de42086140228fe9fbcf0beeda59
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06927292B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes