Hydrochloric Acid → HCID 66777111, compound

HRID 2091033Notes

Reaction equation

HRID 2091033 reaction equation
[CH:1]1([CH:7]([NH:20][C:21]2[CH:29]=[CH:28][C:24](C(O)=O)=[CH:23][CH:22]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CNC[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl.[CH3:63][N:64]([CH3:67])[CH:65]=[O:66]>C(N(CC)CC)C>[CH:1]1([CH:7]([NH:20][C:21]2[CH:29]=[CH:28][C:24]([C:65]([N:64]([CH3:67])[CH2:63][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:66])=[CH:23][CH:22]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]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 66778638HCID 66778638, compound

Product 1

HCID 66777111HCID 66777111, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 4-{[cyclohexyl(5-methoxy-3-methyl-1-benzofuran-2-yl)methyl]amino}benzoic acid (745 mg) synthesized above, ethyl 3-(methylamino)propanoate (298 mg), 1-hydroxybenzotriazole monohydrate (348 mg), triethylamine (633 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (435 mg), and the mixture was stirred at room temperature for overnight then at 50° C. for 3 hr. 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 (801 mg, 84%) as a pale-brown solid.

Workup

  1. waitat 50° C. for 3 hr
  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 (55% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6b2eb8c0ee0249a48e3fda58d8786611
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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