4-Methoxybenzenesulfonyl chloride → HCID 21936986, compound

HRID 746486Notes

Reaction equation

HRID 746486 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[C:13]1([CH:19]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:20][CH2:21][N:22]([CH:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=2)=[O:24])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCCC1>[C:42]1([CH:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:20][CH2:21][N:22]([CH:36]2[CH2:37][CH2:38][N:39]([S:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)(=[O:11])=[O:10])[CH2:40][CH2:41]2)[C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:34])([F:33])[F:35])[CH:27]=2)=[O:24])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

4

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 21936992HCID 21936992, compound

Product 1

HCID 21936986HCID 21936986, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

27.5 mg (100 μmol, 2 eq.) of morpholinomethyl resin is preswollen in anhydrous tetrahydrofuran, then 4-methoxyphenylsulphonyl chloride (15.5 mg, 0.075 mmol, 1.5 eq.) then N-(3,3-diphenylpropyl)-N-(4-piperidinyl)-N′-[3-(trifluoromethyl)phenyl] urea (24.3 mg, 0.05 mmol) are added. The mixture is agitated overnight. The aminomethyl (20 mg) and SAX ion exchange resins are added and the mixture is agitated overnight. The resins are filtered and rinsed with dichloromethane. The oil obtained after evaporation is passed through a silica gel cartridge (500 mg, Interchim) eluting with ethyl acetate in order to obtain 18 mg (yield=56%) of a white solid after concentration.

Workup

  1. stirringthe mixture is agitated overnight
  2. filtrationThe resins are filtered
  3. washrinsed with dichloromethane
  4. customThe oil obtained
  5. customafter evaporation
  6. washeluting with ethyl acetate in order

Sources & evidence

ORD record
ord-332410f50b78438aba72fe2afa34297e
Source dataset
uspto-grants-2008_07
Patent number
US07393861B2

Reaction notes

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