Benzenesulfonyl chloride → HCID 57447086, compound

HRID 2366705Notes

Reaction equation

HRID 2366705 reaction equation
[CH3:1][C:2]1[N:3]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:20])[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:14]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.C1(S(Cl)(=O)=O)C=CC=CC=1.[OH-].[NH4+:49]>>[CH3:1][C:2]1[N:3]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:20])[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([NH2:49])[C:5]=2[N:14]=1

Participants

5

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 57447089HCID 57447089, compound

Product 1

HCID 57447086HCID 57447086, compound

Procedure

2-Methyl-1-(5-morpholin-4-yl-5-oxopentyl)-1H-imidazo[4,5-c]quinoline (8.4 g, 24 mmol) was treated with mCPBA (7.19 g, 41.7 mmol), ammonium hydroxide (40 mL), and benzenesulfonyl chloride (5.93 mL, 46.5 mmol) according to the method described in Part D of Example 36. The crude product was purified by column chromatography on silica gel (eluting with 90:10 dichloromethane:methanol). The resulting product was triturated with 10% aqueous sodium hydroxide, isolated by filtration, washed with water, and dried overnight in a vacuum oven to provide 0.487 g of 2-methyl-1-(5-morpholin-4-yl-5-oxopentyl)-1H-imidazo[4,5-c]quinolin-4-amine as an off-white powder, mp 218-219° C.

Workup

  1. customThe crude product was purified by column chromatography on silica gel (eluting with 90:10 dichloromethane:methanol)
  2. customThe resulting product was triturated with 10% aqueous sodium hydroxide
  3. customisolated by filtration
  4. washwashed with water
  5. customdried overnight in a vacuum oven

Sources & evidence

ORD record
ord-6978a1263df1453bb6cf009d50e20718
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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