Dichloromethane → HCID 69586435, compound

HRID 985111Notes

Reaction equation

HRID 985111 reaction equation
[OH:1][C@H:2]1C(=O)C2C=CN3C=C(C)N=C3C=2N[C@@H:3]1C1C=CC=CC=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:39](Cl)(=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41].[OH:46][C@H:47]1[C@@H:56]([O:57][CH2:58][CH2:59][O:60][CH2:61]COC)[C:55]2[CH:54]=[CH:53][N:52]3[C:65](C)=[C:66](C)[N:67]=[C:51]3[C:50]=2[NH:49][C@@H:48]1[C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1.Cl[CH2:77][Cl:78]>>[C:2]([N:49]1[C:50]2[C:51]3=[N:67][C:66]([CH3:65])=[C:77]([Cl:78])[N:52]3[CH:53]=[CH:54][C:55]=2[C@@H:56]([O:57][CH2:58][CH2:59][O:60][CH3:61])[C@H:47]([O:46][C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])[C@H:48]1[C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)(=[O:1])[CH3:3]

Participants

7

Reactant 6

HCID 6344Dichloromethane2×HCID 8471Triethylamine2×HCID 218852-Dimethylaminopyridine2×HCID 62493Pivaloyl chloride2×HCID 10194462(7S,8R,9R)-8-Hydroxy-7-[2-(2-methoxyethoxy)ethoxy]-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridineHCID 69586463(8R,9R)-8-Hydroxy-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

Product 1

HCID 69586435HCID 69586435, compound

Conditions

Temperature
0 °C

Procedure

To a of 0° C. cooled solution of 10.5 g (35.8 mmol) (8R,9R)-8-hydroxy-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one in dichloromethane (110 ml) is added 5.70 ml (41.2 mmol) triethylamine, 0.22 g (1.80 mmol) dimethylaminopyridine and 5.10 ml (41.2 mmol) pivaloyl chloride dissolved in dichloromethane (10 ml). The reaction is stirred for 2 h at 0° C. and warmed up to 25° C. and stirred for further 24 h. Afterwards 5.70 ml (41.2 mmol) triethylamine, 0.22 9 (1.80 mmol) dimethylaminopyridine and 5.10 ml (41.2 mmol) pivaloyl chloride are added to this mixture and it is stirred for 18 h at 25° C. Subsequently the reaction is quenching by adding of water (100 ml). The organic layer is separated, washed with ammonia solution, washed with water two times, dried over sodium sulphate and evaporated in vacuo. The crude product is crystallised from 2-propanol to provide 12.1 g (32.06 mmol/90%) of the title compound as a colourless solid with a melting point of 145-147° C. (2-propanol).

Workup

  1. temperaturewarmed up to 25° C.
  2. stirringstirred for further 24 h
  3. stirringis stirred for 18 h at 25° C
  4. customSubsequently the reaction is quenching
  5. additionby adding of water (100 ml)
  6. customThe organic layer is separated
  7. washwashed with ammonia solution
  8. washwashed with water two times
  9. dry with materialdried over sodium sulphate
  10. customevaporated in vacuo
  11. customThe crude product is crystallised from 2-propanol

Sources & evidence

ORD record
ord-12c8331822a6405b9b8f09007814b266
Source dataset
uspto-grants-2005_03
Patent number
US06869949B2

Reaction notes

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