2-Methylpentane → HCID 89690069, compound

HRID 517888Notes

Reaction equation

HRID 517888 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[CH2:26][CH2:25][CH2:24][NH:23][C:12]2=[N:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[F:22].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+].CCCC(C)C>ClCCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[CH2:26][CH2:25][CH2:24][N:23]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:12]2=[N:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[F:22]

Participants

6

Reactant 4

HCID 78922-MethylpentaneHCID 77609Heptanoic acid, 7-oxo-, ethyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 89689877HCID 89689877, compound

Product 1

HCID 89690069HCID 89690069, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture comprising 2,3-bis(2,4-difluorophenyl)-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine (Intermediate CC) (310 mg, 0.863 mmol) in 1,2-dichloroethane (10 ml) was added to ethyl 7-oxoheptanoate (446 mg, 2.59 mmol) and stirred at RT for 15 mins. Sodium triacetoxyborohydride (914 mg, 4.31 mmol) was added and stirring continued at RT for 3 days. The mixture was heated to 60° C. for 3 h and allowed to cool to RT. The resulting mixture was applied to a pre-wet (iso-hexane) Isolute® cartridge (silica) and eluted with 20-33% EtOAc in iso-hexane to afford the titled compound;

Workup

  1. stirringstirring
  2. waitcontinued at RT for 3 days
  3. temperatureThe mixture was heated to 60° C. for 3 h
  4. temperatureto cool to RT
  5. washeluted with 20-33% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-e243e5bc370244299cadfe1dbfbc9e9e
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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