4-Toluenesulfonyl chloride → HCID 66619871, compound

HRID 415564Notes

Reaction equation

HRID 415564 reaction equation
[N:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]1[N:13]3[CH2:14][CH2:15][N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:12]3=[N:11][C:4]=1[CH:5]=[N:6]2.C1C=C(Cl)C=C(C(OO)=O)C=1.[OH-].[NH4+:36].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl>[NH2:36][C:5]1[C:4]2[N:11]=[C:12]3[N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:14][N:13]3[C:3]=2[C:2]2[C:7](=[CH:8][CH:9]=[CH:10][N:1]=2)[N:6]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acid2×HCID 66619900HCID 66619900, compound

Product 1

HCID 66619871HCID 66619871, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 9,10-dihydro-8H-imidazo[1′,2′:1,2]imidazo[4,5-c][1,5]naphthyridine-8-carboxylate (1 g, 3 mmol) in dichloromethane (100 mL) was treated with MCPBA (1 g, 77% purity), and the reaction was stirred for two hours. Analysis by LC/MS indicated the presence of starting material, and additional MCPBA (1 g) was added. The next day, the reaction cooled in an ice bath and was treated with 100 mL of concentrated ammonium hydroxide. The reaction was stirred for several minutes, and then p-toluenesulfonyl chloride (730 mg, 3.8 mmol) was added. The reaction was stirred for several minutes, removed from the ice bath, and stirred for three hours at room temperature. Water was added, and the mixture was extracted with dichloromethane. The combined organic fractions were purified by automated flash chromatography on silica gel (eluting with a gradient of 2% ammonium hydroxide methanol as the polar component in dichloromethane). The resulting oil was triturated in diethyl ether to provide a yellow solid, which was isolated by filtration to provide 0.64 g of tert-butyl 6-amino-9,10-dihydro-8H-imidazo[1′,2′:1,2]imidazo[4,5-c][1,5]naphthyridine-8-carboxylate.

Workup

  1. additionwas added
  2. temperatureThe next day, the reaction cooled in an ice bath
  3. stirringThe reaction was stirred for several minutes
  4. stirringThe reaction was stirred for several minutes
  5. customremoved from the ice bath
  6. stirringstirred for three hours at room temperature
  7. additionWater was added
  8. extractionthe mixture was extracted with dichloromethane
  9. customThe combined organic fractions were purified by automated flash chromatography on silica gel (
  10. washeluting with a gradient of 2% ammonium hydroxide methanol as the polar component in dichloromethane)
  11. customThe resulting oil was triturated in diethyl ether
  12. customto provide a yellow solid
  13. customwhich was isolated by filtration

Sources & evidence

ORD record
ord-a863791b1d714751944d2481af999383
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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