Sodium hydride → HCID 67205423, compound

HRID 547301Notes

Reaction equation

HRID 547301 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[H][H].Cl[CH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][N:19]1[C:31]2[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N:24]=[C:23]([NH2:32])[C:22]=2[N:21]=[C:20]1[CH2:33][CH2:34][CH3:35]>CN(C=O)C.O>[CH2:33]([C:20]1[N:19]([CH2:18][CH2:17][O:16][CH2:15][CH2:14][CH2:13][S:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[C:31]2[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N:24]=[C:23]([NH2:32])[C:22]=2[N:21]=1)[CH2:34][CH3:35]

Participants

7

Reactant 4

HCID 24758Sodium hydride2×HCID 67203500HCID 67203500, compoundHCID 178418361HCID 178418361, compoundHCID 178418616HCID 178418616, compound2×

Product 1

HCID 67205423HCID 67205423, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere 2-mercaptopyridine (1.23 g, 11.1 mmol) was added to a suspension of sodium hydride (0.41 g of 60%, 10 mmol) in DMF (30 mL). After hydrogen evolution had ceased, 1-[2-(3-chloropropoxy)ethyl]-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (3.20 g, 9.23 mmol) was added. After 2 hours analysis by HPLC indicated that starting material remained. 2-Mercaptopyridine (0.30 g) and sodium hydride (0.10 g) were added. After 3.5 hours the reaction mixture was poured into water with rapid stirring. The resulting brown solid was isolated by filtration and then triturated with diethyl ether to provide 3.71 g of 2-propyl-1-(2-{3-[(pyridin-2-yl)thio]propoxy}ethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a solid.

Workup

  1. customThe resulting brown solid was isolated by filtration
  2. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-4840976d43d04ea5b5b3e8715687afb9
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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