Dichloromethane → HCID 68685438, compound

HRID 2245301Notes

Reaction equation

HRID 2245301 reaction equation
[NH2:1][CH2:2][C:3]([CH3:7])([CH3:6])[CH2:4][OH:5].CCN(C(C)C)C(C)C.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([NH:26][CH2:27][C:28]2[S:32][C:31]([S:33](Cl)(=[O:35])=[O:34])=[CH:30][CH:29]=2)=[O:25])=[CH:20][CH:19]=1.C(Cl)Cl>CN(C=O)C>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]([NH:26][CH2:27][C:28]2[S:32][C:31]([S:33](=[O:35])(=[O:34])[NH:1][CH2:2][C:3]([CH3:7])([CH3:6])[CH2:4][OH:5])=[CH:30][CH:29]=2)=[O:25])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 1173261-Propanol, 3-amino-2,2-dimethyl-HCID 27357135-((4-Chlorobenzamido)methyl)thiophene-2-sulfonyl chloride

Product 1

HCID 68685438HCID 68685438, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 2 equivalents of 3-Amino-2,2-dimethyl-propan-1-ol (1.0 g, 10 mmol) in DMF in the presence of 2 equivalents of DIEA (1.7 ml, 10 mMol) is added a solution of sulfonylchloride (1b) (1.75 g, 5 mMol, 1 equivalent) in DMF. The reaction mixture is stirred for 12 h at room temperature. DCM is added and any excess of amine is extracted into 0.1N HCl solution. The organic phase is washed with brine and dried over MgSO4. 4-Chloro-N-[5-(3-hydroxy-2,2-dimethyl-propylsulfamoyl)-thiophen-2-ylmethyl]-benzamide (compound of formula XII) is obtained after evaporation of the solvent. LC-MS analysis and NMR analysis showed that the compound was pure enough to carry on the next step.

Workup

  1. extractionany excess of amine is extracted into 0.1N HCl solution
  2. washThe organic phase is washed with brine
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-04829a1866234c81b1666141bcc680bf
Source dataset
uspto-grants-2010_03
Patent number
US07683078B2

Reaction notes

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