Benzoic acid, 3-(chlorosulfonyl)- → 3-{[({3'-[(1-Methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)amino]sulfonyl}benzoic Acid

HRID 564571Notes

Reaction equation

HRID 564571 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]2[CH:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][NH2:22])[CH:16]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:4][CH2:3]1.Cl[S:24]([C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30]([OH:32])=[O:31])(=[O:26])=[O:25]>C(Cl)Cl>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]2[CH:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][NH:22][S:24]([C:27]4[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=4)[C:30]([OH:32])=[O:31])(=[O:26])=[O:25])[CH:16]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 57813254({3'-[(1-Methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)amine

Product 1

HCID 578134563-{[({3'-[(1-Methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)amino]sulfonyl}benzoic AcidYield 89.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{3′-[(1-methyl-4-piperidinyl)methyl]-3-biphenylyl}methanamine (0.0589 g, 0.2 mmol) in DCM (2 mL) was added TEA (0.0606 mL, 0.4 mmol) and then 3-(chlorosulfonyl)benzoic acid (0.0441 g, 0.2 mmol) whereupon the reaction was stirred at room temperature for 17 h. The reaction mixture was concentrated on a Glas-Col evaporator, purified using a Gilson HPLC (with 0.1% TFA), and concentrated to afford 0.0861 g (57%) of the title compound. LC-MS m/z 479 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated on a Glas-Col evaporator
  2. custompurified
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-273ca680d8904558902b654539f581ce
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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