Hydrochloric Acid → HCID 66778251, compound

HRID 2091142Notes

Reaction equation

HRID 2091142 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH:11]([NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=1)[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:30][NH:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].O.ON1C2C=CC=CC=2N=N1.Cl>CN(C)C=O.C(N(CC)CC)C>[CH3:30][N:31]([C:25]([C:24]1[CH:28]=[CH:29][C:21]([NH:20][CH:11]([C:3]2[O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:2]=2[CH3:1])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:22][CH:23]=1)=[O:26])[CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 541480Ethyl 3-(methylamino)propanoateHCID 27960291-Hydroxybenzotriazole hydrateHCID 66778701HCID 66778701, compound

Product 1

HCID 66778251HCID 66778251, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 4-{[1-(3-methyl-1-benzofuran-2-yl)-2-phenoxyethyl]amino}benzoic acid (100 mg) synthesized in Example A94(3), ethyl 3-(methylamino)propanoate (50.8 mg), 1-hydroxybenzotriazole monohydrate (59.3 mg), triethylamine (54 μL) and N,N-dimethylformamide (10 mL) 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (74.2 mg) was added, and the mixture was stirred overnight at room temperature. 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 (50% ethyl acetate/hexane) to give the title object compound (82.5 mg, 64%) as a yellow oil.

Workup

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-81f16f22e33d4c8ab71cc0594162256a
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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