Triethylamine → HCID 178481068, compound

HRID 2118255Notes

Reaction equation

HRID 2118255 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH2:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]([OH:22])=O)[CH2:16][CH2:15]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.CCN=C=NCCCN(C)C.CCN(CC)CC.[CH3:43][N:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1>C(Cl)Cl.O>[CH3:43][N:44]1[CH2:49][CH2:48][N:47]([C:20]([C@H:17]2[CH2:16][CH2:15][C@H:14]([CH2:13][NH:12][S:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:23])([F:1])[F:24])=[CH:4][CH:5]=3)(=[O:10])=[O:11])[CH2:19][CH2:18]2)=[O:22])[CH2:46][CH2:45]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 531671-MethylpiperazineHCID 178525723HCID 178525723, compound

Product 1

HCID 178481068HCID 178481068, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

200 mg (0.54 mmol) of trans-4-[(4-trifluoromethyl-benzenesulfonylamino)-methyl]-cyclohexanecarboxylic acid, 210 mg (1.09 mmol, 2 eq) of EDCI, 221 mg (2.2 mmol, 4 eq) of Et3N and 274 mg (2.74 mmol, 5 eq) of 1-methyl-piperazine were dissolved in 5 mL of CH2Cl2. After 70 h reaction at RT, 1 mL of H2O was added and the reaction mixture was stirred vigorously for 1 h. The organic phase was separated, the aqueous phase was extracted with 10 mL of CH2Cl2 and the combined organic phases were washed with H2O and brine. After drying over anhydrous Na2SO4, the organic phase was evaporated. The residue was chromatographed on silicagel with CH2Cl2:MeOH:25% NH4OH (9:1:0.1) as eluent. 120 mg (49%) of trans-N-[4-(4-methyl-piperazine-1-carbonyl)-cyclohexylmethyl]-4-trifluoromethyl-benzenesulfonamide were obtained as colorless amorphous solid, MS: 448 (MH+).

Workup

  1. customAfter 70 h reaction at RT
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with 10 mL of CH2Cl2
  4. washthe combined organic phases were washed with H2O and brine
  5. dry with materialAfter drying over anhydrous Na2SO4
  6. customthe organic phase was evaporated
  7. customThe residue was chromatographed on silicagel with CH2Cl2

Sources & evidence

ORD record
ord-6f00382d8b2043f5902398176a5f0bf1
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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