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

HRID 723413Notes

Reaction equation

HRID 723413 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:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[C:9](=[O:27])[C:8]=3[CH:7]=[CH:6][N:5]2[CH:28]=1.[C:29](Cl)(=[O:31])[CH3:30].C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:29]([N:12]1[C:13]2[C:4]3=[N:3][C:2]([CH3:1])=[CH:28][N:5]3[CH:6]=[CH:7][C:8]=2[C:9](=[O:27])[C@H:10]([O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:23])[CH3:24])[C@H:11]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 6367Acetyl chloride2×HCID 8471Triethylamine2×HCID 69586205(8R,9R)-2-methyl-9-phenyl-8-pivaloyloxy-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

Product 1

HCID 69586437(8R,9R)-10-Acetyl-2-methyl-9-phenyl-8-pivaloyloxy-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a of 0° C. cooled solution of 7.00 g (18.5 mmol) (8R,9R)-2-methyl-9-phenyl-8-pivaloyloxy-7.8.9.10-tetrahydroimidazo[1.2-h][1.7]naphthyridin-7-one in toluene (70 ml) is added 4.10 ml (55.5 mmol) acetyl chloride and 7.70 ml (55.5 mmol) triethylamine and the reaction mixture is stirred for 1 h at 0° C. Afterwards further 4.10 ml (55.5 mmol) acetyl chloride and 7.70 ml (55.5 mmol) triethylamine are added to the reaction mixture and it is warmed up to 25° C. and stirred at this temperature for 1 h. Subsequently the reaction is quenched by adding of saturated aqueous ammonium chloride solution. This mixture is extracted twice with dichloromethane. The combined organic layers are washed with brine, dried over sodium sulphate and evaporated in vacuo. The crude product is crystallised from diethyl ether to provide 5.4 g (12.7 mmol/70%) of the title compound as a colourless solid with a melting point of 168–169° C. (diethyl ether).

Workup

  1. temperatureis warmed up to 25° C.
  2. stirringstirred at this temperature for 1 h
  3. customSubsequently the reaction is quenched
  4. additionby adding of saturated aqueous ammonium chloride solution
  5. extractionThis mixture is extracted twice with dichloromethane
  6. washThe combined organic layers are washed with brine
  7. dry with materialdried over sodium sulphate
  8. customevaporated in vacuo
  9. customThe crude product is crystallised from diethyl ether

Sources & evidence

ORD record
ord-615587a34ffc43e6a4ab53383756e63a
Source dataset
uspto-grants-2006_11
Patent number
US07141567B2

Reaction notes

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