Triethylamine → HCID 67542103, compound

HRID 219822Notes

Reaction equation

HRID 219822 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[N:13]([CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:14][CH2:15][CH3:16])[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[CH2:8]([O:7][C:5](=[O:6])[C:4]1[CH:10]=[CH:11][C:12]([N:13]([CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:14][CH2:15][CH3:16])=[C:2]([NH:1][S:29]([CH3:28])(=[O:31])=[O:30])[CH:3]=1)[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67528421Ethyl 3-amino-4-[isobutyl(propyl)amino]benzoate

Product 1

HCID 67542103HCID 67542103, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3-amino-4-[isobutyl(propyl)amino]benzoate (5 g, 0.0179 mol) in dry DCM (50 mL) was added triethyl amine (7.24 g, 0.0716 mol) at RT. Methane sulphonyl chloride (2.67 g, 0.0233 mol) was added in drops at 0° C. The reaction mixture was stirred at RT for 4 h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in water, extracted with ethylacetate (2×75 mL), washed with 0.5M HCl, brine, dried over sodium sulphate and evaporated to afford the title compound as a yellow oil (6 g, 93%). 1H NMR (DMSO-d6, 400 MHz) δ 8.45 (s, 1H), 7.86 (s, 1H), 7.65 (m, 1H), 7.28 (m, 1H), 4.28 (m, 2H), 3.09 (s, 3H) 3.01 (m, 2H), 2.86 (m, 2H), 1.68 (m, 1H), 1.42 (m, 2H), 1.28 (m, 3H), 0.80 (m, 9H). LC/MS (Method A): 357.0 (M+H)+. HPLC (Method B) Rt 5.09 min (purity: 94.40%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with ethylacetate (2×75 mL)
  4. washwashed with 0.5M HCl, brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-969f0eab5e264e2d87ee176d7aa7ed98
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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