Dimethylformamide → (R)-N-(benzoyl)-3-methyl-N'-[(1-methyl-7-azaindol-3-yl)-oxoacetyl]-piperazine

HRID 2184250Notes

Reaction equation

HRID 2184250 reaction equation
[H-].[Na+].[C:3]([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:29])[C:18]([C:20]2[C:28]3[C:23](=[N:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)=[O:19])[C@H:13]([CH3:30])[CH2:12]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:31]N(C=O)C>>[C:3]([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:29])[C:18]([C:20]2[C:28]3[C:23](=[N:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH3:31])[CH:21]=2)=[O:19])[C@H:13]([CH3:30])[CH2:12]1)(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 5495793Piperazine, 4-benzoyl-1-(1,2-dioxo-2-(1H-pyrrolo(2,3-b)pyridin-3-yl)ethyl)-2-methyl-, (2R)-

Product 1

HCID 507780(R)-N-(benzoyl)-3-methyl-N'-[(1-methyl-7-azaindol-3-yl)-oxoacetyl]-piperazineYield 24%

Procedure

NaH (2 mg, 60% pure, 0.05 mmol) was added to a solution of compound 5a (10 mg, 0.027 mmol) in DMF. After 30 minutes, Mel (5 mg, 0.035 mmol) was injected into the mixture via syringe. The reaction mixture was stirred for 8 hours at room temperature and quenched with methanol. The mixture was partitioned between ethyl acetate (2 ml) and H2O (2 ml). The aqueous phase was extracted with EtOAc (3×2 ml). The organic layers were combined, dried over anhydrous MgSO4 and concentrated in vacuo to give a crude product which was purified using a Shimadzu automated preparative HPLC System to give compound 21a (2.5 mg, 24%).

Workup

  1. customMel (5 mg, 0.035 mmol) was injected into the mixture via syringe
  2. customquenched with methanol
  3. customThe mixture was partitioned between ethyl acetate (2 ml) and H2O (2 ml)
  4. extractionThe aqueous phase was extracted with EtOAc (3×2 ml)
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give a crude product which
  8. customwas purified

Sources & evidence

ORD record
ord-188785c4e2d24e1890f1e4309aaef278
Source dataset
uspto-grants-2005_05
Patent number
US06900323B2

Reaction notes

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