Heptanoic acid, 7-oxo-, ethyl ester → HCID 131731626, compound

HRID 517887Notes

Reaction equation

HRID 517887 reaction equation
[C:1]([O:4][CH:5]1[C:14]2[C:9](=[N:10][C:11]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[N:13]=2)[NH:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2].O=[CH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O>[CH3:1][O:4][CH:5]1[C:14]2[C:9](=[N:10][C:11]([C:22]3[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=3)=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[N:13]=2)[N:8]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])[CH2:7][CH2:6]1.[C:1]([O:4][CH:5]1[C:14]2[C:9](=[N:10][C:11]([C:22]3[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=3)=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[N:13]=2)[N:8]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 77609Heptanoic acid, 7-oxo-, ethyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 66665498HCID 66665498, compound

Product 2

HCID 131731626HCID 131731626, compoundHCID 131733356HCID 131733356, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a solution of rac-2,3-di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazin-8-yl acetate ((prepared according to the preparation procedures disclosed in PCT patent application PCT/EP2011/062028, Intermediate HF) (209 mg, 0.560 mmol) in DCE (dry) (10 ml) was added ethyl 7-oxoheptanoate (289 mg, 1.679 mmol) followed by sodium triacetoxy borohydride (356 mg, 1.679 mmol). The mixture was left to stir overnight at room temperature under an atmosphere of nitrogen. The resulting mixture was diluted with water (20 ml) and extracted with EtOAc (3×20 ml). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was passed through an Isolute® SCX-2 SPE cartridge and was loaded onto a primed (with MeOH 20 ml) SCX-2 cartridge. The methanolic ammonia fractions were concentrated under reduced pressure to afford the titled compound as a mixture with rac-ethyl 7-(8-acetoxy-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate; The mixture was used in the next step without further purification;

Workup

  1. customaccording to the preparation procedures
  2. waitThe mixture was left
  3. extractionextracted with EtOAc (3×20 ml)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. concentrationThe methanolic ammonia fractions were concentrated under reduced pressure

Sources & evidence

ORD record
ord-0c7eda62604b4c0e8c3b812964f02b46
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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