Sodium hydride → HCID 23395876, compound

HRID 431620Notes

Reaction equation

HRID 431620 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH:15]([CH2:18][CH3:19])[CH2:16][OH:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[H-].[Na+].Br[CH2:23][C:24]([O:26][CH3:27])=[O:25]>CN(C)C=O>[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH:15]([CH2:18][CH3:19])[CH2:16][O:17][CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 21936606HCID 21936606, compound

Product 1

HCID 23395876HCID 23395876, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol (25 mg, 0.0975 mmol) was placed in a 2 dram (7.4 mL) vial. Sodium hydride (5 mg of a 60% dispersion in mineral oil, 0.117 mmol) and N,N-dimethylformamide (1 mL) were added. The vial was placed on a sonicator for 15 minutes at ambient temperature to allow the alkoxide to form. Methyl bromoacetate (11 μL, 0.117 mmol) was added. The reaction was sonicated at ambient temperature for 1.5 hours. The reaction mixture was analyzed by LC/MS to confirm the formation of the desired product. The reaction mixture was purified by semi-preparative HPLC using Method A Mass Measurement (Da.): Theoretical mass=328.1535, Measured mass=328.1534.

Workup

  1. customto form
  2. customThe reaction was sonicated at ambient temperature for 1.5 hours

Sources & evidence

ORD record
ord-387dec669fbb4dc98f1421def88dfc24
Source dataset
uspto-grants-2003_12
Patent number
US06660747B2

Reaction notes

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