Hydrochloric Acid → HCID 57951114, compound

HRID 1919808Notes

Reaction equation

HRID 1919808 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8](=[O:14])[CH2:9][CH2:10][C:11]([OH:13])=O)[CH:5]=[CH:6][CH:7]=1.[F:15][C:16]([F:26])([F:25])[O:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([C:8](=[O:14])[CH2:9][CH2:10][C:11]([NH:22][C:21]2[CH:23]=[CH:24][C:18]([O:17][C:16]([F:15])([F:25])[F:26])=[CH:19][CH:20]=2)=[O:13])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 6008484-(Trifluoromethoxy)anilineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27591244-(3-fluorophenyl)-4-oxobutanoic acid

Product 1

HCID 57951114HCID 57951114, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir 4-(3-fluoro-phenyl)-4-oxo-butyric acid [C.A. 69797-46-2] (J. Med. Chem. (1983) 26 381) (1.96 g, 10 mmol), 4-trifluoromethoxyaniline (1.77 g, 10 mmol) and O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) (3.5 g, 11 mmol) in dimethylformamide (30 mL). Add triethylamine (2.02 g, 20 mmol). Stir at room temperature for 48 hours. Pour into dilute aqueous HCl (250 mL) and extract into ethyl acetate. Wash the organic phase three times with water, dry over anhydrous magnesium sulfate, evaporate and purify on a silica gel column (dichloromethane-ethyl acetate) to give the titled compound (3.13 g, 88% yield) MS (m/z): 356 (M+1).

Workup

  1. extractionextract into ethyl acetate
  2. washWash the organic phase three times with water
  3. dry with materialdry over anhydrous magnesium sulfate
  4. customevaporate
  5. custompurify on a silica gel column (dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-5d0a5bf2fbd14c42987d846a48a3f04a
Source dataset
uspto-grants-2012_05
Patent number
US08168659B2

Reaction notes

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