4-Toluenesulfonyl chloride → HCID 58923859, compound

HRID 1364069Notes

Reaction equation

HRID 1364069 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[CH2:12]([O:19][C:20]1[CH:29]=[C:28]2[C:23]([C:24]3[N:32]4[CH2:33][CH2:34][CH2:35][N:36]([S:38]([CH3:41])(=[O:40])=[O:39])[CH2:37][C:31]4=[N:30][C:25]=3[CH:26]=[N:27]2)=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[NH4+:43].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[CH2:12]([O:19][C:20]1[CH:29]=[C:28]2[C:23]([C:24]3[N:32]4[CH2:33][CH2:34][CH2:35][N:36]([S:38]([CH3:41])(=[O:40])=[O:39])[CH2:37][C:31]4=[N:30][C:25]=3[C:26]([NH2:43])=[N:27]2)=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acid2×HCID 66958571HCID 66958571, compound

Product 1

HCID 58923859HCID 58923859, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

mCPBA (2.96 g of 77% purity, 13.2 mmol) was added to a solution of 3-(benzyloxy)-9-(methylsulfonyl)-9,10,11,12-tetrahydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinoline (4.648 g, 11 mmol) in chloroform (20 mL), and the reaction was stirred for 10 minutes. Additional mCPBA (1.5 g) was added and the reaction was monitored for disappearance of the starting substrate by thin-layer chromatography (TLC). Ammonium hydroxide (20 mL) was then added and the reaction was stirred for five minutes before the rapid addition of p-toluenesulfonyl chloride (2.31 g, 12.1 mmol). The reaction was stirred overnight at ambient temperature. The organic layer was separated, washed with ammonium hydroxide, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting with 2 N ammonia in methanol/chloroform in a 43-minute gradient from 1:99 to 25:75) and recrystallization from isopropanol and dried in a vacuum oven at 65° C. to afford 1.1 g of 3-(benzyloxy)-9-(methylsulfonyl)-9,10,11,12-tetrahydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine as brown crystals, mp 235-236° C.

Workup

  1. stirringThe reaction was stirred overnight at ambient temperature
  2. customThe organic layer was separated
  3. washwashed with ammonium hydroxide
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (
  7. washeluting with 2 N ammonia in methanol/chloroform in a 43-minute gradient from 1:99 to 25:75) and
  8. customrecrystallization from isopropanol
  9. customdried in a vacuum oven at 65° C.

Sources & evidence

ORD record
ord-8ac9f611c8af4e24a38cf22b36c481ad
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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