Trifluoroacetic acid → biphenyl-4-carboxylic acid (2-oxo-2-piperazin-1-yl-ethyl)-amide TFA salt

HRID 1178009Notes

Reaction equation

HRID 1178009 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].C(OC([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:38])[CH2:22][NH:23][C:24]([C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:28][CH:27]=2)=[O:25])[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[OH:7][C:1]([C:3]([F:6])([F:5])[F:4])=[O:2].[O:38]=[C:21]([N:18]1[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]1)[CH2:22][NH:23][C:24]([C:26]1[CH:27]=[CH:28][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:30][CH:31]=1)=[O:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 311221914-{2-[(Biphenyl-4-carbonyl)-amino]-acetyl}-piperazine-1-carboxylicacid tert-butyl ester

Product 1

HCID 131728551biphenyl-4-carboxylic acid (2-oxo-2-piperazin-1-yl-ethyl)-amide TFA saltYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (3.6 mL) was added to a stirred solution of 4-{2-[(biphenyl-4-carbonyl)-amino]-acetyl}-piperazine-1-carboxylicacid tert-butyl ester (1.7 g, 4.01 mmol) in DCM (18 mL) at 0-4° C. and the resulting mixture was stirred at this temperature for 3 hrs. The reaction mixture was concentrated to afford 1.67 g (94.8% yield) of biphenyl-4-carboxylic acid (2-oxo-2-piperazin-1-yl-ethyl)-amide TFA salt. LC-MS purity: 85.4%,

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-bf90bacfbbc440ae9bce5684c2259fa6
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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