Water → HCID 178483789, compound

HRID 2118257Notes

Reaction equation

HRID 2118257 reaction equation
[CH3:1][N:2]([CH2:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([C:23]([OH:25])=O)[CH2:19][CH2:18]1)[S:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)(=[O:5])=[O:4].S(Cl)(Cl)=O.[CH3:30][N:31]([CH3:36])[CH2:32][CH2:33][NH:34][CH3:35].O>C(Cl)Cl.N1C=CC=CC=1>[CH3:30][N:31]([CH3:36])[CH2:32][CH2:33][N:34]([CH3:35])[C:23]([C@H:20]1[CH2:19][CH2:18][C@H:17]([CH2:16][N:2]([CH3:1])[S:3]([C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:13])([F:15])[F:14])=[CH:8][CH:7]=2)(=[O:5])=[O:4])[CH2:22][CH2:21]1)=[O:25]

Participants

7

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 178484088HCID 178484088, compound

Product 1

HCID 178483789HCID 178483789, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 200 mg (0.53 mmol) trans-4-{[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-methyl}-cyclohexanecarboxylic acid and 125 mg (1.05 mmol, 2 eq) of thionyl chloride in 1 mL of dry CH2Cl2 were heated at 50° C. for 1 h, then evaporated and dissolved in 1 mL of CH2Cl2. This solution was added to 269 mg (2.54 mmol, 5 eq) of N,N,N′-trimethylethylenediamine in 1 mL of pyridine at 0° C. and stirred for 2 h at RT. Subsequently the reaction mixture was poured on a mixture of ice and water and extracted with 3 portions of 15 mL of CH2Cl2. The combined organic phases were washed with H2O, diluted HCl, saturated aqueous NaHCO3 solution and brine, then dried over anhydrous Na2SO4 and finally evaporated. The residue was chromatographed on silicagel with CH2Cl2:MeOH:25% NH4OH (9:1:0.1) as eluent. 195 mg (79.8%) of trans-4-{[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-methyl}-cyclohexanecarboxylic acid (2-dimethylamino-ethyl)-methyl-amide were obtained as colorless amorphous solid, MS: 464 (MH+).

Workup

  1. customevaporated
  2. dissolutiondissolved in 1 mL of CH2Cl2
  3. extractionextracted with 3 portions of 15 mL of CH2Cl2
  4. washThe combined organic phases were washed with H2O, diluted HCl, saturated aqueous NaHCO3 solution and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customfinally evaporated
  7. customThe residue was chromatographed on silicagel with CH2Cl2

Sources & evidence

ORD record
ord-b3e8768de49947a294e724c849e4a6e0
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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