Dimethylformamide → HCID 68511346, compound

HRID 1877188Notes

Reaction equation

HRID 1877188 reaction equation
[CH:1]1([CH:7]([NH:26][C:27]2[CH:35]=[CH:34][C:30](C(O)=O)=[CH:29][CH:28]=2)[C:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[O:10][C:9]=2[CH2:23][S:24][CH3:25])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CNC[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41].Cl.C(N=C=NCCCN(C)C)C.O.OC1C2N=NNC=2C=CC=1.[CH3:68][N:69]([CH3:72])[CH:70]=[O:71]>C(OCC)(=O)C.C(N(CC)CC)C>[CH:1]1([CH:7]([NH:26][C:27]2[CH:28]=[CH:29][C:30]([C:70]([N:69]([CH3:72])[CH2:68][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[O:71])=[CH:34][CH:35]=2)[C:8]2[CH:12]=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:17][CH:18]=3)[O:10][C:9]=2[CH2:23][S:24][CH3:25])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68512188HCID 68512188, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 68511346HCID 68511346, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-[(cyclohexyl{2-[(methylsulfanyl)methyl]-5-[4-(trifluoromethyl)phenyl]furan-3-yl}methyl)amino]benzoic acid (1.0 g), ethyl 3-(methylamino)propanoate (0.3 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.5 g), hydroxybenzotriazole monohydrate (0.4 g) and triethylamine (0.3 mL) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 4 hr. Ethyl acetate was added, the mixture was washed with saturated aqueous sodium hydrogen carbonate solution and water, and the organic layer was dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (10% ethyl acetate/hexane to 40% ethyl acetate/hexane) to give the title compound (1.2 g, 100%) as an amorphous compound.

Workup

  1. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate solution and water
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (10% ethyl acetate/hexane to 40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-87682aa150c448b3ba000da8521f0e46
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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