4-Toluenesulfonyl chloride → HCID 66620124, compound

HRID 415560Notes

Reaction equation

HRID 415560 reaction equation
C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[Br:12][C:13]1[CH:22]=[C:21]2[C:16]([C:17]3[N:26]4[CH2:27][CH2:28][CH2:29][N:30]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:25]4=[N:24][C:18]=3[CH:19]=[N+:20]2[O-])=[CH:15][CH:14]=1.[OH-].[NH4+:39]>ClCCl.O>[NH2:39][C:19]1[C:18]2[N:24]=[C:25]3[N:30]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:29][CH2:28][CH2:27][N:26]3[C:17]=2[C:16]2[C:21](=[CH:22][C:13]([Br:12])=[CH:14][CH:15]=2)[N:20]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 66620274HCID 66620274, compound

Product 1

HCID 66620124HCID 66620124, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

p-Toluenesulfonyl chloride (441 mg, 2.3 mmol) was added to a mixture of tert-butyl 3-bromo-5-oxido-10,11-dihydropyrimido[1′,2′:1,2]imidazo[4,5-c]quinoline-8(9H)-carboxylate (0.97 g, 2.3 mmol), dichloromethane (30 mL), and concentrated ammonium hydroxide (3 mL), and the reaction was stirred overnight at room temperature. Water and dichloromethane were added. The aqueous layer was separated and extracted four times with dichloromethane. The combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with a gradient of 2% ammonium hydroxide/methanol in dichloromethane), and the resulting product was recrystallized from 1,2-dichloroethane and hexanes to provide 0.16 g of tert-butyl 6-amino-3-bromo-10,11-dihydropyrimido[1′,2′:1,2]imidazo[4,5-c]quinoline-8(9H)-carboxylate.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted four times with dichloromethane
  3. dry with materialThe combined organic fractions were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel (
  7. washeluting with a gradient of 2% ammonium hydroxide/methanol in dichloromethane), and the resulting product
  8. customwas recrystallized from 1,2-dichloroethane and hexanes

Sources & evidence

ORD record
ord-6807eac927044d0ab6e1ebcf8cc2eefa
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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