Water → HCID 89689894, compound

HRID 517913Notes

Reaction equation

HRID 517913 reaction equation
[CH3:1][C:2]1([OH:26])[C:11]2[C:6](=[N:7][C:8]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)[N:10]=2)[NH:5][CH2:4][CH2:3]1.O=[CH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl>[OH:26][C:2]1([CH3:1])[C:11]2[C:6](=[N:7][C:8]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:9]([C:12]3[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=3)[N:10]=2)[N:5]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 77609Heptanoic acid, 7-oxo-, ethyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 89689897HCID 89689897, compound2×

Product 1

HCID 89689894HCID 89689894, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 8-methyl-2,3-di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazin-8-ol (Intermediate G) (290 mg, 0.840 mmol) in DCE (10 ml) was added ethyl 7-oxoheptanoate (434 mg, 2.52 mmol) followed by sodium triacetoxyborohydride (534 mg, 2.52 mmol). The reaction mixture was left to stir overnight at room temperature under an atmosphere of nitrogen and then water was added (20 ml). The product was extracted with EtOAc (2×20 ml) and the combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to give a crude brown oil. Purification of the crude product by C18 reverse phase chromatography eluting with water/acetonitrile afforded the title compound;

Workup

  1. waitThe reaction mixture was left
  2. extractionThe product was extracted with EtOAc (2×20 ml)
  3. dry with materialthe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give a crude brown oil
  7. customPurification of the crude product by C18 reverse phase chromatography
  8. washeluting with water/acetonitrile

Sources & evidence

ORD record
ord-616552303cfc41139160a5fe29f98de9
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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