Diisopropylethylamine → HCID 16043214, compound

HRID 2245634Notes

Reaction equation

HRID 2245634 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)[CH3:2].C(N(CC)C(C)C)(C)C.Cl.[NH2:27][CH2:28][C:29]1([C:35]2[CH:40]=[CH:39][C:38]([S:41]([NH:44][C:45]3[S:46][C:47]([CH:50]([CH3:52])[CH3:51])=[N:48][N:49]=3)(=[O:43])=[O:42])=[CH:37][CH:36]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>CN(C)C=O>[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:5]=1[C:6]([NH:27][CH2:28][C:29]1([C:35]2[CH:36]=[CH:37][C:38]([S:41](=[O:43])(=[O:42])[NH:44][C:45]3[S:46][C:47]([CH:50]([CH3:52])[CH3:51])=[N:48][N:49]=3)=[CH:39][CH:40]=2)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1)=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 224943272-Ethoxy-4-(trifluoromethyl)benzoic acidHCID 68617696HCID 68617696, compound

Product 1

HCID 16043214HCID 16043214, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

55 mg of 2-ethoxy-4-trifluoromethyl-benzoic acid (example 1g), 85 mg Totu and 100 mg N,N-diisopropylethylamine were dissolved in cold dimethylformamide. After 30 minutes 100 mg of 4-(1-aminomethyl-cyclohexyl)-N-(5-isopropyl-[1,3,4]thiadiazol-2-yl)-benzenesulfonamide hydrochloride were added and the mixture stirred over night. After evaporation of the solvent the residue was purified by chromatography on silica gel with the eluents dichloromethane:methanol=98:2 to obtain 134 mg of an oily product.

Workup

  1. customAfter evaporation of the solvent the residue
  2. customwas purified by chromatography on silica gel with the eluents dichloromethane

Sources & evidence

ORD record
ord-8df3379c60dc42dbbe8540dab1002e08
Source dataset
uspto-grants-2010_03
Patent number
US07683181B2

Reaction notes

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