Dichloromethane → HCID 21915000, compound

HRID 2117950Notes

Reaction equation

HRID 2117950 reaction equation
O[CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([NH:18][C:19](=[O:21])[CH3:20])[S:16][CH:17]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5].CC[N:24](CC)CC.C(Cl)Cl.CS(Cl)(=O)=O>O.CO.C(Cl)(Cl)Cl>[NH2:24][CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([NH:18][C:19](=[O:21])[CH3:20])[S:16][CH:17]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21914707HCID 21914707, compound

Product 1

HCID 21915000HCID 21915000, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21584188Chloroform methanolSolvent

Procedure

N-(4-{4-[(2-Hydroxyethyl)sulfonyl]phenyl}-1,3-thiazol-2-yl)acetamide (200 mg), Et3N (0.102 ml) and CH2Cl2 (4 ml) were combined under N2 atmosphere, and then MsCl (0.05 ml) was added to the suspension at 0° C. The reaction mixture was stirred at r.t. for 2 hours. MeOH/CHCl3 and water were added to the mixture, and the mixture was extracted. The organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residual solid (221.6 mg) was suspended in CH3CN (10 ml), and then 28% ammonia solution (0.5 ml) was added to the suspension at 0° C. The reaction mixture was stirred at r.t. for 15 hours, and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel with [MeOH/CHCl3 (1:30), then NH4OH/MeOH/CHCl3 (1:10:60)] as an eluent, and triturated with EtOH/ethyl ether to give N-(4-{4-[(2-aminoethyl)sulfonyl]phenyl}-1,3-thiazol-2-yl)acetamide (60.4 mg) as an off-white solid.

Workup

  1. extractionthe mixture was extracted
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. addition28% ammonia solution (0.5 ml) was added to the suspension at 0° C
  6. stirringThe reaction mixture was stirred at r.t. for 15 hours
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography over silica gel with [MeOH/CHCl3 (1:30)
  9. customNH4OH/MeOH/CHCl3 (1:10:60)] as an eluent, and triturated with EtOH/ethyl ether

Sources & evidence

ORD record
ord-8c858cca78a74965953b804dcaa2883f
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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