Methyl p-toluenesulfonate → HCID 86621632, compound

HRID 547521Notes

Reaction equation

HRID 547521 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:25])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[CH:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:26][O:27][S:28]([C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=1)(=[O:30])=[O:29]>CN(C=O)C>[CH3:37][C:34]1[CH:33]=[CH:32][C:31]([S:28]([O-:30])(=[O:29])=[O:27])=[CH:36][CH:35]=1.[CH3:26][N+:22]1[CH:21]=[CH:20][C:19]([NH:18][C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([C:11]([NH:10][C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)=[O:25])[CH:13]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 59457990HCID 59457990, compound

Product 1

HCID 86621632HCID 86621632, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound C4 (1.92 g, 5.73 mmol) was suspended in DMF (10 mL), methyl-p-toluenesulfonate (15 mL) was added, and the mixture was stirred at room temperature for 18 h. Solvent was removed under reduced pressure and the residue was dissolved in warm MeOH (10 mL), then diluted with EtOAc. Some of the MeOH was boiled off, and the solution was then refrigerated for 18 h. The resulting precipitate was filtered, and washed with EtOAc to give essentially pure C5 (2.90 g, 97%), which was used without further purification. 1H NMR [(CD3)2SO] δ10.85 (s, 1 H, CONH), 10.60 (s, 1 H, NH), 8.33-8.27 (m, 4 H, H-3′,5′ & py H-2,6), 8.08-8.30 (m, 2 H, H-2′,6′), 7.94-7.89 (m, 2 H, H-2″ 4″), 7.69 (t, J=7.9 Hz, 1 H, H-5″), 7.60-7.57 (m, 1 H, H-6″), 7.48-7.45 (m, 2 H, H-3, 5), 7.22 (d, J=7.5 Hz, 2 H, p-tol H-2,6), 7.20 (d, J=8.1 Hz, 2 H, p-tol H-3,5), 3.99 (s, 3 H, N+CH3), 1.99 (s, 3 H, CH3).

Workup

  1. customSolvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in warm MeOH (10 mL)
  3. additiondiluted with EtOAc
  4. waitthe solution was then refrigerated for 18 h
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with EtOAc

Sources & evidence

ORD record
ord-cceb7666ffbc4730a5fe823fd357f1fe
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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