4-Toluenesulfonyl chloride → HCID 87741738, compound

HRID 1027871Notes

Reaction equation

HRID 1027871 reaction equation
[NH2:1][C:2]1[N:17]=[C:16]([OH:18])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:4]=2[N:3]=1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[NH2:1][C:2]1[N:17]=[C:16]([O:18][S:25]([C:22]2[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=2)(=[O:27])=[O:26])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 178508872HCID 178508872, compound

Product 1

HCID 87741738HCID 87741738, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Example 20B (950 mg, 2.4 mmol) in CH2Cl2 (30 mL) was added para-toluenesulfonyl chloride (1.09 g, 5.7 mmol), 4-dimethylaminopyridine (50 mg, 0.41 mmol) and triethylamine (1.1 mL. 7.9 mmol) and the mixture was stirred at room temperature for 16 hours. The mixture was diluted with CH2Cl2 (100 mL), washed with H2O, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified on silica gel eluting with EtOAc:hexanes (25:75) to provide the title compound.

Workup

  1. washwashed with H2O
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified on silica gel eluting with EtOAc:hexanes (25:75)

Sources & evidence

ORD record
ord-24b183110aa74a32afc9e28dedc13d9f
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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