Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → N-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]-2-(2-bromophenyl)-2-(4-chlorophenylaminocarbonylamino)-acetamide

HRID 2244988Notes

Reaction equation

HRID 2244988 reaction equation
CN1CCN=C1C1C=CC([NH:13][C:14](=[O:34])[CH:15]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Br:33])[NH:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[O:18])=CC=1.[CH3:35][N:36]1[CH2:41][CH2:40][CH:39]([N:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)[CH2:38][CH2:37]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[CH3:35][N:36]1[CH2:37][CH2:38][CH:39]([N:42]2[CH2:47][CH2:46][N:45]([NH:13][C:14](=[O:34])[CH:15]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[Br:33])[NH:16][C:17]([NH:19][C:20]3[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=3)=[O:18])[CH2:44][CH2:43]2)[CH2:40][CH2:41]1

Participants

5

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 5663241-(1-Methyl-4-piperidinyl)piperazineHCID 11692377N-[4-(1-methyl-4,5-dihydro-1H-imidazol-2-yl)phenyl]-2-(2-bromophenyl)-2-(4-chlorophenylaminocarbonylamino)-acetamide

Product 1

HCID 11649811N-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]-2-(2-bromophenyl)-2-(4-chlorophenylaminocarbonylamino)-acetamideYield 88.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-bromophenyl)-2-(4-chlorophenylaminocarbonylamino)-acetic acid (from EXAMPLE 77, 30 mg, 0.078 mmol), 1-(1-methylpiperidin-4-yl)piperazine (purchased from Oakwood products, 21 mg, 0.11 mmol) and TEA (0.0-44 mL, 0.31 mmol) in DMF (3 mL), BOP (69 mg, 0.16 mmol) was added. After being stirred at room temperature for 1 h, the mixture was concentrated in vacuo. The residue was purified by HPLC to give the titled compound as a powder (39 mg). MS 548.3 and 550.3 (M+H, Cl+Br pattern).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-0a3693eb3f9147488a60513d67a07c3d
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

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