1-Methylpiperazine → HCID 178427945, compound

HRID 2218415Notes

Reaction equation

HRID 2218415 reaction equation
[Cl:1][C:2]1[C:3]([CH3:21])=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14](F)=[C:13]([N+:18]([O-])=O)[CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>CCOC(C)=O>[Cl:1][C:2]1[C:3]([CH3:21])=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:26]4[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]4)=[C:13]([NH2:18])[CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 178427944HCID 178427944, compound

Product 1

HCID 178427945HCID 178427945, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Crude 6-chloro-2-(4-fluoro-3-nitrophenyl)-7-methyl-3H-imidazo[4,5-b]pyridine (Example 252) (333 mg) and 1-methylpiperazine (1.0 ml) were mixed and left at room temperature for 15 min, whereupon it was diluted with EtOAc (50 ml) and washed with water (100 ml). The aqueous phase was extracted with EtOAc (50 ml) and the combined organic phase was evaporated in vacuo. The yellow oily residue was dissolved in methanol (100 ml) and hydrogenated in a Parr apparatus (Raney nickel, 60 psi, 5 h). The catalyst was removed by filtration and the solvent removed in vacuo. The residue was purified by semi-preparative HPLC-C18 affording the product as a trifluoroacetate. The salt was dissolved in EtOAc (10 ml) and washed with aqueous 10% NaHCO3 solution (5 ml), brine (5 ml) and dried (MgSO4). Evaporation of the solvent yielded the product as an off-white powder (67 mg, 25%).

Workup

  1. washwashed with water (100 ml)
  2. extractionThe aqueous phase was extracted with EtOAc (50 ml)
  3. customthe combined organic phase was evaporated in vacuo
  4. dissolutionThe yellow oily residue was dissolved in methanol (100 ml) and hydrogenated in a Parr apparatus (Raney nickel, 60 psi, 5 h)
  5. customThe catalyst was removed by filtration
  6. customthe solvent removed in vacuo
  7. customThe residue was purified by semi-preparative HPLC-C18

Sources & evidence

ORD record
ord-8e692c79c48b4730bb32d53a40ae8c4d
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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