Triethylamine → 3-{[({3'-[(4-{[(1,1-Dimethyl ethyl)oxy]carbonyl}-1-piperazinyl)methyl]-6-fluoro-3-biphenylyl}methyl)amino]sulfonyl}benzoic acid

HRID 564565Notes

Reaction equation

HRID 564565 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].[NH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([F:42])=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]3[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]3)[CH:23]=2)[CH:21]=1.CCN(CC)CC>C(Cl)Cl>[CH3:41][C:38]([O:37][C:35]([N:32]1[CH2:33][CH2:34][N:29]([CH2:28][C:24]2[CH:23]=[C:22]([C:20]3[C:19]([F:42])=[CH:18][CH:17]=[C:16]([CH2:15][NH:14][S:2]([C:5]4[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=4)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3])[CH:21]=3)[CH:27]=[CH:26][CH:25]=2)[CH2:30][CH2:31]1)=[O:36])([CH3:39])[CH3:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 578132811,1-Dimethylethyl 4-{[5'-(aminomethyl)-2'-fluoro-3-biphenylyl]methyl}-1-piperazinecarboxylate

Product 1

HCID 578134033-{[({3'-[(4-{[(1,1-Dimethyl ethyl)oxy]carbonyl}-1-piperazinyl)methyl]-6-fluoro-3-biphenylyl}methyl)amino]sulfonyl}benzoic acidYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(chlorosulfonyl)benzoic acid (0.0331 g, 0.15 mmol) in DCM (1.5 mL) was added 1,1-dimethylethyl 4-{[5′-(aminomethyl)-2′-fluoro-3-biphenylyl]methyl}-1-piperazinecarboxylate (0.060 g, 0.15 mmol), and Et3N (0.0211 mL, 0.15 mmol). The resulting mixture was stirred at room temperature for 1 h before it was concentrated and purified using a Gilson HPLC to afford the title compound 0.0374 g (43%). LC-MS m/z 584 (M+H)+.

Workup

  1. concentrationwas concentrated
  2. custompurified

Sources & evidence

ORD record
ord-976b3adcf2aa4bb4bcfba629c9843587
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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