Sodium hydride → HCID 56631766, compound

HRID 1681628Notes

Reaction equation

HRID 1681628 reaction equation
[C:1]1([C:7]2[N:18]3[C:10]([C:11]4[NH:12][CH:13]=[N:14][C:15]=4[N:16]([CH2:20][CH2:21][CH3:22])[C:17]3=[O:19])=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:25](I)[CH2:26][CH3:27].[Cl-].[NH4+]>CN(C=O)C>[CH2:20]([N:16]1[C:15]2[N:14]=[CH:13][N:12]([CH2:25][CH2:26][CH3:27])[C:11]=2[C:10]2=[N:9][N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:18]2[C:17]1=[O:19])[CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 336431-IodopropaneHCID 135702816135446-00-3

Product 1

HCID 56631766HCID 56631766, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After 500 mg (1.70 mmol) of Compound 30 obtained in Example 30 was dissolved in 5 ml of N,N'-dimethylformamide, 81.6 mg (2.04 mmol) of 60% sodium hydride was added to the solution at 0° C. 15 minutes after, 0.25 ml (2.51 mmol) of propyl iodide was added to the reaction solution at 0° C. The solution was stirred at room temperature for 30 minutes. After 20 ml of saturated ammonium chloride was added to the reaction solution at 0° C., the mixture was extracted 3 times with 30 ml of chloroform. The extracts were combined and washed with a saturated sodium chloride aqueous solution. After drying over anhydrous sodium sulfate, the solvent was eva.oprated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: 2% methanol/chloroform) to afford 434 mg (yield, 76%) of Compound 35 as white needles.

Workup

  1. extractionthe mixture was extracted 3 times with 30 ml of chloroform
  2. washwashed with a saturated sodium chloride aqueous solution
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. customThe residue was purified by silica gel column chromatography (eluting solvent: 2% methanol/chloroform)
  5. customto afford

Sources & evidence

ORD record
ord-7373665f987b4058915a8599bb5f0741
Source dataset
uspto-grants-1992_12
Patent number
US05173492

Reaction notes

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