Dimethylformamide → HCID 66778108, compound

HRID 2091049Notes

Reaction equation

HRID 2091049 reaction equation
[CH:1]1([CH:7]([NH:21][C:22]2[CH:30]=[CH:29][C:25](C(O)=O)=[CH:24][CH:23]=2)[C:8]2[O:9][C:10]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:11]=3[C:12]=2[CH2:13][O:14][CH3:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CNC[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl-].[NH4+].[CH3:65][N:66]([CH3:69])[CH:67]=[O:68]>C(N(CC)CC)C>[CH:1]1([CH:7]([NH:21][C:22]2[CH:30]=[CH:29][C:25]([C:67]([N:66]([CH3:69])[CH2:65][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:68])=[CH:24][CH:23]=2)[C:8]2[O:9][C:10]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:11]=3[C:12]=2[CH2:13][O:14][CH3:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66778332HCID 66778332, compound

Product 1

HCID 66778108HCID 66778108, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 4-({cyclohexyl[5-fluoro-3-(methoxymethyl)-1-benzofuran-2-yl]methyl}amino)benzoic acid (200 mg) synthesized in Example A47(7), ethyl 3-(methylamino)propanoate (95.6 mg), 1-hydroxybenzotriazole monohydrate (112 mg), triethylamine (203 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (140 mg), and the mixture was stirred at room temperature overnight. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the reaction 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 (197 mg, 77%) as a pale-yellow oil.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe reaction 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-7441e8f266e44354aaf8291e82a7988b
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

Loading…