4-Toluenesulfonyl chloride → HCID 67052344, compound

HRID 599429Notes

Reaction equation

HRID 599429 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[Cl:12][CH2:13][C:14]1[N:15]([CH2:27][CH2:28][CH2:29][NH:30][C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])[C:16]2[C:25]3[N:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]=[CH:18][C:17]=2[N:26]=1.[OH-].[NH4+:37].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl.[Cl-].[Na+].O>[NH2:37][C:18]1[C:17]2[N:26]=[C:14]([CH2:13][Cl:12])[N:15]([CH2:27][CH2:28][CH2:29][NH:30][C:31](=[O:35])[CH:32]([CH3:33])[CH3:34])[C:16]=2[C:25]2[N:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N:19]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 67052376HCID 67052376, compound

Product 1

HCID 67052344HCID 67052344, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

mCPBA (0.985 g, 5.71 mmol) was added to a suspension of N-{3-[2-(chloromethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]propyl}-2-methylpropanamide (1.41 g, 4.08 mmol) in chloroform (20 mL). The reaction mixture was allowed to stir for 4 hours at room temperature. Concentrated ammonium hydroxide (5 mL) followed by p-toluenesulfonyl chloride (0.854 g, 4.48 mmol) were added and the mixture was stirred at room temperature for 1 hour. The mixture was diluted with chloroform (25 mL) and brine (40 mL) and transferred to a separatory funnel. The aqueous layer was extracted with chloroform (20 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated to afford a tan solid. Trituration with methanol and isolation by filtration afforded 0.670 g of N-{3-[4-amino-2-(chloromethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]propyl}-2-methylpropanamide.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. customtransferred to a separatory funnel
  4. extractionThe aqueous layer was extracted with chloroform (20 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a tan solid
  9. filtrationTrituration with methanol and isolation by filtration

Sources & evidence

ORD record
ord-ee50d880178c4911994bebd6529b0035
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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