Ammonium Chloride → HCID 25166710, compound

HRID 1177907Notes

Reaction equation

HRID 1177907 reaction equation
[Cl-].[NH4+].[O:3]=[C:4]([N:24]1[CH2:29][CH2:28][N:27]([C:30](=[O:41])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37]([F:40])([F:39])[F:38])[CH2:26][CH2:25]1)[CH2:5][NH:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=2)=[CH:11][CH:10]=1)=[O:8]>C1COCC1.O.[Fe]>[O:3]=[C:4]([N:24]1[CH2:25][CH2:26][N:27]([C:30](=[O:41])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37]([F:39])([F:40])[F:38])[CH2:28][CH2:29]1)[CH2:5][NH:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=2)=[CH:11][CH:10]=1)=[O:8]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 59559663HCID 59559663, compound

Product 1

HCID 25166710HCID 25166710, compoundYield 49.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ammonium chloride (74 mg, 1.4 mmol) was added to a stirred solution of 3′-nitro-biphenyl-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide (prepared by the method as described above) (123 mg, 0.2 mmol) in a mixture of THF (6 mL) and H2O (4 ml). Iron powder (77 mg) was then added and the resulting mixture at reflux temperature for 3 hrs. The mixture was filtered, and the filtrate was concentrated. The residue was dissolved in EtOAc, washed with 5% aqueous NaHCO3 solution, followed by saturated brine solution. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford 69 mg (49.3% yield) of 3′-Amino-biphenyl-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 92.88%. 1H NMR (CDCl3): δ 7.9 (d, 2H), 7.8-7.7 (bd, 1H), 7.7-7.6 (m, 4H), 7.6-7.55 (bs, 1H), 7.4-7.3 (d, 1H), 7.2 (d, 1H), 7.0 (d, 1H), 6.9 (t, 1H), 6.8 (d, 1H), 4.38-4.3 (m, 1H), 4.3-4.22 (m, 1H), 4.08-3.96 (bd, 2H), 3.94-3.86 (bs, 1H), 3.84-3.64 (m, 4H), 3.64-3.32 (m, 2H), 3.52-3.46 (d, 1H), 3.44-3.4 (t, 1H), 3.3-3.2 (bs, 2H).

Workup

  1. customprepared by the method
  2. temperaturethe resulting mixture at reflux temperature for 3 hrs
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in EtOAc
  6. washwashed with 5% aqueous NaHCO3 solution
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe84cb795f8344178e0f7c15b2e5bd32
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

Loading…