Acetic Acid → N-(4-{4-[Diethylcarbamoyl-(3-fluoro-phenyl)-methyl]-piperazin-1-yl}-3-fluoro-phenyl)-2-ethyl-butyramide

HRID 1927604Notes

Reaction equation

HRID 1927604 reaction equation
[CH2:1]([CH:3]([CH2:31][CH3:32])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([CH:19]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[C:20](O)=[O:21])[CH2:15][CH2:14]2)=[C:9]([F:30])[CH:8]=1)=[O:5])[CH3:2].CO[C:35](=O)[CH:36]([N:44]1CCN(C2C=CC(NC(=O)C(CC)CC)=CC=2F)[CH2:46][CH2:45]1)C1C=CC=C(F)C=1.[OH-].[K+].CC(O)=O>O.CO.O>[CH2:36]([N:44]([CH2:45][CH3:46])[C:20]([CH:19]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1)[N:16]1[CH2:15][CH2:14][N:13]([C:10]2[CH:11]=[CH:12][C:7]([NH:6][C:4](=[O:5])[CH:3]([CH2:1][CH3:2])[CH2:31][CH3:32])=[CH:8][C:9]=2[F:30])[CH2:18][CH2:17]1)=[O:21])[CH3:35]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 16667233HCID 16667233, compoundHCID 69304344{4-[4-(2-Ethyl-butyrylamino)-2-fluoro-phenyl]-piperazin-1-yl}-(3-fluoro-phenyl)-acetic acid

Product 1

HCID 16667279N-(4-{4-[Diethylcarbamoyl-(3-fluoro-phenyl)-methyl]-piperazin-1-yl}-3-fluoro-phenyl)-2-ethyl-butyramide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

{4-[4-(2-Ethyl-butyrylamino)-2-fluoro-phenyl]-piperazin-1-yl}-(3-fluoro-phenyl)-acetic acid. A mixture of {4-[4-(2-ethyl-butyrylamino)-2-fluoro-phenyl]-piperazin-1-yl}-(3-fluoro-phenyl)-acetic acid methyl ester (0.22 g, 0.47 mmol) in water/MeOH (1:4, 5 mL) was treated with KOH (0.095 g, 1.70 mmol) and the resulting mixture was heated at reflux for 24 h. The mixture was cooled to rt and acidified to pH 6.5 with AcOH. The mixture was diluted with water and extracted with DCM. The organic layer was dried (Na2SO4) and concentrated to yield the title compound (0.24 g), which was carried forward to the next step.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 24 h
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2d8e1da77f8f4028b8b2850060e14dbd
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

Loading…