4-Toluenesulfonyl chloride → 6-amino-12-methyl-8,9,11,12-tetrahydro-10H-[1,4]diazepino[1',2':1,2]imidazo[4,5-c]quinolin-10-one

HRID 221566Notes

Reaction equation

HRID 221566 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:12][CH:13]1[N:19]2[C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=[CH:22][C:21]=3[N:30]=[C:18]2[CH2:17][NH:16][C:15](=[O:31])[CH2:14]1.[OH-].[NH4+:33].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[NH2:33][C:22]1[C:21]2[N:30]=[C:18]3[CH2:17][NH:16][C:15](=[O:31])[CH2:14][CH:13]([CH3:12])[N:19]3[C:20]=2[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chloride2×HCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 6715682312-methyl-8,9,11,12-tetrahydro-10H-[1,4]diazepino[1',2':1,2]imidazo[4,5-c]quinolin-10-one

Product 1

HCID 671567716-amino-12-methyl-8,9,11,12-tetrahydro-10H-[1,4]diazepino[1',2':1,2]imidazo[4,5-c]quinolin-10-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

MCPBA (2.73 g of 77% purity, 16 mmol) was added to a solution of 12-methyl-8,9,11,12-tetrahydro-10H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinolin-10-one (1.3 g, 4.9 mmol) in chloroform (20 mL), and the reaction mixture was stirred for 15 minutes at room temperature. Concentrated ammonium hydroxide (30 mL) and p-toluenesulfonyl chloride (1.12 g, 5.86 mmol) were sequentially added, and the resulting mixture was stirred at room temperature for two hours. An analysis by LC/MS indicated the presence of the 5N-oxide, and additional p-toluenesulfonyl chloride (1 equivalent) was added. The mixture was stirred at room temperature overnight. The organic layer was separated and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting with 0% to 15% 2 N methanolic ammonia in chloroform over a period of 42 minutes) followed by recrystallization from acetonitrile to provide 389 mg of 6-amino-12-methyl-8,9,11,12-tetrahydro-10H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinolin-10-one.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for two hours
  2. additionwas added
  3. stirringThe mixture was stirred at room temperature overnight
  4. customThe organic layer was separated
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (
  7. washeluting with 0% to 15% 2 N methanolic ammonia in chloroform over a period of 42 minutes)
  8. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-1dd9cba21bd445f183b5a0be7aa99343
Source dataset
uspto-grants-2012_06
Patent number
US08207162B2

Reaction notes

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