Hydrochloric Acid → Ethyl 3-{[(4-{[1-(5-chloro-3-methyl-1-benzofuran-2-yl)-3-methylbutyl]amino}phenyl)carbonyl](methyl)amino}propanoate

HRID 2091167Notes

Reaction equation

HRID 2091167 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]([NH:15][C:16]3[CH:24]=[CH:23][C:19](C(O)=O)=[CH:18][CH:17]=3)[CH2:11][CH:12]([CH3:14])[CH3:13])=[C:7]([CH3:25])[C:6]=2[CH:26]=1.CNC[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.[CH3:60][N:61]([CH3:64])[CH:62]=[O:63]>C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]([NH:15][C:16]3[CH:24]=[CH:23][C:19]([C:62]([N:61]([CH3:64])[CH2:60][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:63])=[CH:18][CH:17]=3)[CH2:11][CH:12]([CH3:13])[CH3:14])=[C:7]([CH3:25])[C:6]=2[CH:26]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 667771684-{[1-(5-Chloro-3-methyl-1-benzofuran-2-yl)-3-methylbutyl]amino}benzoic acid

Product 1

HCID 66778481Ethyl 3-{[(4-{[1-(5-chloro-3-methyl-1-benzofuran-2-yl)-3-methylbutyl]amino}phenyl)carbonyl](methyl)amino}propanoateYield 85%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 4-{[1-(5-chloro-3-methyl-1-benzofuran-2-yl)-3-methylbutyl]amino}benzoic acid (180 mg) synthesized in Example A100(3), ethyl 3-(methylamino)propanoate (95.2 mg), 1-hydroxybenzotriazole monohydrate (111 mg), triethylamine (202 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (139 mg), and the mixture was stirred at room temperature for 2.5 days. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (55% ethyl acetate/hexane) to give the title object compound (199 mg, 85%) as a colorless oil.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (55% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-89ed88751db840df80c766933417f5b6
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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