Acetic Acid → HCID 54554155, compound

HRID 2217011Notes

Reaction equation

HRID 2217011 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].Cl[CH2:19]Cl.[CH3:21][N:22](C=O)C>C1COCC1>[CH3:19][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 sodium hydride (60% in oil, 20 mg, 0.5 mmol). After stirring for 20 min, Example 27 (34 mg, 0.15 mmol) was added and the mixture was stirred at rt overnight. The mixture was neutralized with acetic acid. Dichloromethane (10 ml) was added to the mixture and the resulting precipitate was collected and washed with small amount of dichloromethane, water and dried in vacuo to give 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 amount of dichloromethane, water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-305728ccaa044fdba8146905611fd679
Source dataset
uspto-grants-2006_09
Patent number
US07112675B2

Reaction notes

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