Trifluoroacetic acid → HCID 59559669, compound

HRID 1177983Notes

Reaction equation

HRID 1177983 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]([N:23]1[CH2:28][CH2:27][N:26]([C:29](=[O:46])[CH2:30][NH:31][C:32]([C:34]2[CH:39]=[CH:38][C:37]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:36][CH:35]=2)=[O:33])[CH2:25][CH2:24]1)=[O:22])(C)(C)C>C(Cl)Cl>[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]([N:23]1[CH2:28][CH2:27][N:26]([C:29](=[O:46])[CH2:30][NH:31][C:32]([C:34]2[CH:39]=[CH:38][C:37]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[CH:36][CH:35]=2)=[O:33])[CH2:25][CH2:24]1)=[O:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59559661HCID 59559661, compound

Product 1

HCID 59559669HCID 59559669, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.6 mL) was added to a stirred cold (0-5° C.) solution of [2-(4-{2-[(Biphenyl-4-carbonyl)-amino]-acetyl}-piperazine-1-carbonyl)-phenyl]-carbamic acid tert-butyl ester (90 mg, 0.165 mmol) in DCM (4 mL). Stirring was continued at same temperature for 4 hr. The mixture was quenched with DIPEA (1.1 ml) and cold water was then added and the product was extracted with DCM and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to get the residue. The obtained residue was purified by column chromatography (using neutral alumina and 100% EtOAc as eluent) to afford 30 mg (40.8% yield) of biphenyl-4-carboxylic acid {2-[4-(2-amino-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide. LCMS Purity: 98.48%. 1H NMR (CDCl3): δ 7.9 (d, 2H), 7.68 (d, 2H), 7.62 (d, 2H), 7.5-7.4 (t, 3H), 7.4 (m, 1H), 7.3 (s, 1H), 7.2 (d, 1H), 7.08 (dd, 1H), 6.8-6.7 (m, 2H), 4.4 (s, 1H), 4.3 (d, 2H), 3.7 (d, 6H), 3.56 (t, 2H), 3.3 (s, 1H).

Workup

  1. customThe mixture was quenched with DIPEA (1.1 ml) and cold water
  2. additionwas then added
  3. extractionthe product was extracted with DCM
  4. washthe organic layer was washed with brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto get the residue
  8. customThe obtained residue was purified by column chromatography (using neutral alumina and 100% EtOAc as eluent)

Sources & evidence

ORD record
ord-af03dbdea40743589e9d78178a648af8
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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