Acetic Acid → HCID 54554155, compound

HRID 433886Notes

Reaction equation

HRID 433886 reaction equation
[CH3:1][C:2]1[N:10]=[C:9]2[C:5]([CH2:6]C(=O)N2)=C[N:3]=1.[H-].[Na+].[C:14]([OH:17])(=[O:16])[CH3:15].[CH2:18](Cl)Cl.[CH3:21][N:22](C=O)C>C1COCC1>[CH3:18][O:16][C:14]([C:15]1[CH:6]=[C:5]2[N:22]([CH:21]=1)[N:3]=[C:2]([CH3:1])[N:10]=[CH:9]2)=[O:17]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 21945830HCID 21945830, compound

Product 1

HCID 54554155HCID 54554155, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-methyl-5,7-diazaoxindole (67 mg, 0.45 mmol) in DMF (2 ml) and THF (1 ml) was added NaH (60% in oil, 20 mg, 0.5 mmol). After stirring for 20 min, Compound E of Example 2 (34 mg, 0.15 mmol) was added. The mixture was stirred at rt overnight and then neutralized with acetic acid. DCM (10 ml) was added and the resulting precipitate was collected and washed with small amounts of DCM and water and then dried in vacuo to give the title compound as an orange solid (32 mg,63%). MS: (M+H)=359

Workup

  1. stirringThe mixture was stirred at rt overnight
  2. customthe resulting precipitate was collected
  3. washwashed with small amounts of DCM and water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-b42d82184dd84715b404dbd1ac8ca4c1
Source dataset
uspto-grants-2003_12
Patent number
US06670357B2

Reaction notes

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