Ammonium Chloride → Ethyl 3-{[(4-{[2-ethyl-1-(3-methyl-1-benzothiophen-2-yl)butyl]amino}phenyl)carbonyl](methyl)amino}propanoate

HRID 2091285Notes

Reaction equation

HRID 2091285 reaction equation
[CH2:1]([CH:3]([CH2:25][CH3:26])[CH:4]([NH:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=1)[C:5]1[S:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]=1[CH3:10])[CH3:2].[CH3:27][NH:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl-].[NH4+]>CN(C)C=O.C(N(CC)CC)C>[CH2:1]([CH:3]([CH2:25][CH3:26])[CH:4]([NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([N:28]([CH3:27])[CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:22])=[CH:23][CH:24]=1)[C:5]1[S:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]=1[CH3:10])[CH3:2]

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 667776494-{[2-Ethyl-1-(3-methyl-1-benzothiophen-2-yl)butyl]amino}benzoic acid

Product 1

HCID 66778165Ethyl 3-{[(4-{[2-ethyl-1-(3-methyl-1-benzothiophen-2-yl)butyl]amino}phenyl)carbonyl](methyl)amino}propanoateYield 77.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 4-{[2-ethyl-1-(3-methyl-1-benzothiophen-2-yl)butyl]amino}benzoic acid (250 mg) synthesized in Example A134(3), ethyl 3-(methylamino)propanoate (134 mg), 1-hydroxybenzotriazole monohydrate (156 mg), triethylamine (284 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (196 mg), and the mixture was stirred at room temperature 2.5 days. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine and saturated aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane) to give the title object compound (253 mg, 77%) as a colorless oil.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine and saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ca473c979df74502bbaaebdd521a1994
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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