Piperazine → HCID 68694582, compound

HRID 2245009Notes

Reaction equation

HRID 2245009 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([NH:13][C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)=[O:15])[C:10]([OH:12])=O.[NH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C([N:32](CC)CC)C.F[P-](F)(F)(F)(F)F.[N:44]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=2N=N1.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[NH:44]1[CH2:49][CH2:50][CH2:51][CH:52]([N:24]2[CH2:29][CH2:28][N:27]([C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])([NH:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)=[O:15])[C:10]([NH2:32])=[O:12])[CH2:26][CH2:25]2)[CH2:47][CH2:48]1

Participants

8

Reactant 5

HCID 4837PiperazineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 68694186HCID 68694186, compound

Product 1

HCID 68694582HCID 68694582, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(2-methoxyphenyl)-2-(4-chlorophenylaminocarbonylamino)-acetic acid (134 mg, 0.400 mmol), piperazine (190 mg, 2.21 mmol) and triethylamine (0.200 mL, 1.44 mmol) in DMF (6.0 mL), BOP (260 mg, 0.587 mmol) was added. After being stirred at room temperature for 30 min, EtOAc and 5% aq. NaHCO3 were added. The organic phase was separated, and concentrated in vacuo. The residue was purified by HPLC to give the amide as a white powder (156 mg).

Workup

  1. customThe organic phase was separated
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-852c1955331147579c0190f893dbc299
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

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