Hydrochloric Acid → HCID 66777150, compound

HRID 2091037Notes

Reaction equation

HRID 2091037 reaction equation
[CH:1]1([CH:7]([NH:19][C:20]2[CH:28]=[CH:27][C:23](C(O)=O)=[CH:22][CH:21]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CNC[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl.[CH3:62][N:63]([CH3:66])[CH:64]=[O:65]>C(N(CC)CC)C>[CH:1]1([CH:7]([NH:19][C:20]2[CH:28]=[CH:27][C:23]([C:64]([N:63]([CH3:66])[CH2:62][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:65])=[CH:22][CH:21]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]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 66779008HCID 66779008, compound

Product 1

HCID 66777150HCID 66777150, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 4-{[cyclohexyl(5-fluoro-3-methyl-1-benzofuran-2-yl)methyl]amino}benzoic acid (1.06 g) synthesized above, ethyl 3-(methylamino)propanoate (438 mg), 1-hydroxybenzotriazole monohydrate (512 mg), triethylamine (930 μL) and N,N-dimethylformamide (20 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (640 mg), and the mixture was stirred at room temperature for 1.5 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 (564 mg, 41%) as a white solid.

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-ea5728c169a4400d966fc9c009f0bf66
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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