4-Toluenesulfonyl chloride → HCID 67052431, compound

HRID 599435Notes

Reaction equation

HRID 599435 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.O=C1C2C(=CC=CC=2)C(=O)[N:14]1[O:23][CH2:24][C:25]1[N:26]([CH2:38][CH2:39][CH2:40][NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[C:27]2[C:36]3[N:35]=[CH:34][CH:33]=[CH:32][C:31]=3[N:30]=[CH:29][C:28]=2[N:37]=1.[OH-].[NH4+:50].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[NH2:50][C:29]1[C:28]2[N:37]=[C:25]([CH2:24][O:23][NH2:14])[N:26]([CH2:38][CH2:39][CH2:40][NH:41][C:42](=[O:48])[O:43][C:44]([CH3:45])([CH3:47])[CH3:46])[C:27]=2[C:36]2[N:35]=[CH:34][CH:33]=[CH:32][C:31]=2[N:30]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 67052435HCID 67052435, compound

Product 1

HCID 67052431HCID 67052431, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

mCPBA (2.33 g, 13.5 mmol) was added to a suspension of tert-butyl 3-(2-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propylcarbamate (4.86 g, 9.67 mmol) in chloroform (50 mL). The reaction mixture was allowed to stir for 4 hours, then concentrated ammonium hydroxide (27 mL) and p-toluenesulfonyl chloride (2.03 g, 10.6 mmol) were added. The reaction mixture was allowed to stir overnight at room temperature, then was filtered. The filtrate was diluted with saturated aqueous sodium bicarbonate (50 mL) and extracted with chloroform (2×40 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated to afford a brown solid that was purified by chromatography using a HORIZON HPFC system (silica gel, gradient elution with 0-30% CMA in chloroform) to afford 1.00 g of tert-butyl 3-{4-amino-2-[(aminooxy)methyl]-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl}propylcarbamate as a yellow solid that contained some minor impurities.

Workup

  1. stirringto stir overnight at room temperature
  2. filtrationwas filtered
  3. additionThe filtrate was diluted with saturated aqueous sodium bicarbonate (50 mL)
  4. extractionextracted with chloroform (2×40 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a brown solid that
  9. customwas purified by chromatography
  10. washa HORIZON HPFC system (silica gel, gradient elution with 0-30% CMA in chloroform)

Sources & evidence

ORD record
ord-126ebde67349422693cffff05729ce38
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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