Triethylamine → N-(2-Ethylamino-5-trifluoromethanesulfonyl-phenyl)-2-(4-methanesulfonyl-phenyl)-acetamide

HRID 1358754Notes

Reaction equation

HRID 1358754 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[CH2:32]([NH:34][C:35]1[C:36]([NH2:48])=[CH:37][C:38]([S:41]([C:44]([F:47])([F:46])[F:45])(=[O:43])=[O:42])=[CH:39][CH:40]=1)[CH3:33]>C(#N)C>[CH2:32]([NH:34][C:35]1[CH:40]=[CH:39][C:38]([S:41]([C:44]([F:45])([F:46])[F:47])(=[O:42])=[O:43])=[CH:37][C:36]=1[NH:48][C:12](=[O:14])[CH2:11][C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=1)[CH3:33]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 5723454-Mesylphenylacetic acidHCID 703518N1-ethyl-4-trifluoromethanesulfonylbenzene-1,2-diamine

Product 1

HCID 9956080N-(2-Ethylamino-5-trifluoromethanesulfonyl-phenyl)-2-(4-methanesulfonyl-phenyl)-acetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-methylsulfonylphenylacetic acid (100 mg, 0.467 mmol) in acetonitrile was added 1-hydroxybenzotriazole (76 mg, 0.56 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carboiimide hydrochloride (108 mg, 0.56 mmol), triethylamine (0.143 mL, 1.03 mmol) and N1-ethyl-4-[(trifluoromethyl)sulfonyl]benzene-1,2-diamine (125 mg, 0.467 mmol). The mixture was stirred at room temperature for overnight. The reaction was extracted with ethyl acetate, washed with water and brine, dried, concentrated and recrystallized from ethyl acetate to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ9.54 (br s, 1H, NH), 7.88 (d, J=8.3 Hz, 2H), 7.75 (d, J=2.1 Hz, 1H), 7.64 (dd, 1H), 7.61 (d, J=8.3 Hz, 2H), 6.90 (d, J=9.0 Hz, 1H), 6.70 (t, J=5.2 Hz, 1H, NH), 3.86 (s, 2H, CH2), 3.31 (s, 3H, CH3), 3.29 (m, 2H, NCH2CH3), 1.20 (t, J=7.1 Hz, 3H, NCH2CH3). MS 465 [M++1].

Workup

  1. extractionThe reaction was extracted with ethyl acetate
  2. washwashed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ba4f8aed8a1b4c888778176ca726eb1f
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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