Dimethylformamide → HCID 68511484, compound

HRID 1877193Notes

Reaction equation

HRID 1877193 reaction equation
[CH:1]1([CH:7]([NH:24][C:25]2[CH:33]=[CH:32][C:28](C(O)=O)=[CH:27][CH:26]=2)[C:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][S:21][CH3:22])=[CH:15][CH:14]=3)[O:10][C:9]=2[CH3:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CNC[CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].Cl.C(N=C=NCCCN(C)C)C.O.OC1C2N=NNC=2C=CC=1.[CH3:66][N:67]([CH3:70])[CH:68]=[O:69]>C(OCC)(=O)C.C(N(CC)CC)C>[CH:1]1([CH:7]([NH:24][C:25]2[CH:26]=[CH:27][C:28]([C:68]([N:67]([CH3:70])[CH2:66][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[O:69])=[CH:32][CH:33]=2)[C:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][S:21][CH3:22])=[CH:15][CH:14]=3)[O:10][C:9]=2[CH3:23])[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 68507969HCID 68507969, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 68511484HCID 68511484, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-{[cyclohexyl(2-methyl-5-{4-[(methylsulfanyl)methoxy]phenyl}furan-3-yl)methyl]amino}benzoic acid (408 mg), ethyl 3-(methylamino)propanoate (134 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (196 mg), hydroxybenzotriazole monohydrate (156 mg) and triethylamine (142 μL) 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 organic layer was dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give ethyl 3-{[(4-{[cyclohexyl(2-methyl-5-{4-[(methylsulfanyl)methoxy]phenyl}furan-3-yl)methyl]amino}phenyl)carbonyl](methyl)amino}propanoate. To ethyl 3-{[(4-{[cyclohexyl(2-methyl-5-{4-[(methylsulfanyl)methoxy]phenyl}furan-3-yl)methyl]amino}phenyl)carbonyl](methyl)amino}propanoate (119 mg) were added ethanol (2 mL), tetrahydrofuran (2 mL) and 1N lithium hydroxide (0.4 mL), and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, and water (10 mL) was added. The mixture was neutralized with 1N hydrochloric acid under ice-cooling, and stirred for 1 hr. The resulting precipitate was collected by filtration and dried to give the title compound (82 mg, 72%).

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. dry with materialthe organic layer was dried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9d7f097599bc4d7eb8e0b3f2fdf82ebc
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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