Water → Ethyl 3-{[(4-{[(5-methoxy-3-methyl-1-benzofuran-2-yl)(phenyl)methyl]amino}phenyl)carbonyl](methyl)amino}-propanoate

HRID 2091215Notes

Reaction equation

HRID 2091215 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([NH:18][C:19]3[CH:27]=[CH:26][C:22](C(O)=O)=[CH:21][CH:20]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:8]([CH3:28])[C:7]=2[CH:29]=1.CNC[CH2:33][C:34]([O:36]CC)=O.[OH2:39].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=N[CH2:56][CH2:57][CH2:58][N:59]([CH3:61])[CH3:60])C.[OH2:62]>CN(C)C=O.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([C:61]([N:59]([CH3:60])[CH2:58][CH2:57][C:56]([O:36][CH2:34][CH3:33])=[O:62])=[O:39])=[CH:26][CH:27]=3)[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[C:8]([CH3:28])[C:7]=2[CH:29]=1

Participants

8

Reactant 5

HCID 962WaterHCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 667776604-{[(5-Methoxy-3-methyl-1-benzofuran-2-yl)(phenyl)methyl]amino}benzoic acid

Product 1

HCID 66777122Ethyl 3-{[(4-{[(5-methoxy-3-methyl-1-benzofuran-2-yl)(phenyl)methyl]amino}phenyl)carbonyl](methyl)amino}-propanoateYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 4-{[(5-methoxy-3-methyl-1-benzofuran-2-yl)(phenyl)methyl]amino}benzoic acid (400 mg) synthesized above, ethyl 3-(methylamino)propanoate (203 mg), 1-hydroxybenzotriazole monohydrate (237 mg), triethylamine (431 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (297 mg), and the mixture was stirred overnight at room temperature. Water 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 (30-70% ethyl acetate/hexane) to give the title object compound (486 mg, 94%) as a pale-brown 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 (30-70% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-003c0fc8e5d243f0beb3730a24ecffbf
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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