Benzenesulfonyl chloride → (3R)-N-{4'-[(Phenylsulfonyl)amino]biphenyl-4-yl}quinuclidine-3-carboxamide hydrochloride

HRID 1661150Notes

Reaction equation

HRID 1661150 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([C@@H:19]3[CH:24]4[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]4)[CH2:20]3)=[O:18])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[C:27]1([S:33]([Cl:36])(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>N1C=CC=CC=1>[ClH:36].[C:27]1([S:33]([NH:3][C:4]2[CH:9]=[CH:8][C:7]([C:10]3[CH:11]=[CH:12][C:13]([NH:16][C:17]([C@@H:19]4[CH:24]5[CH2:23][CH2:22][N:21]([CH2:26][CH2:25]5)[CH2:20]4)=[O:18])=[CH:14][CH:15]=3)=[CH:6][CH:5]=2)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 67427707(3R)-N-(4'-Aminobiphenyl-4-yl)quinuclidine-3-carboxamide dihydrochloride

Product 1

HCID 11283387(3R)-N-{4'-[(Phenylsulfonyl)amino]biphenyl-4-yl}quinuclidine-3-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 80 mg (0.20 mmol) of ((3R)—N-(4′-aminobiphenyl-4-yl)quinuclidine-3-carboxamide dihydrochloride (Example 7A) and 71.7 mg (0.41 mmol) of phenylsulfonyl chloride in 1.0 ml of pyridine is stirred at room temperature for 18 h. The reaction mixture is concentrated in vacuo and the residue is purified by preparative HPLC. The product fractions are concentrated, mixed with 3 ml of 1 N hydrochloric acid, again concentrated and dried under high vacuum. 52 mg (51.5% of theory) of the title compound are obtained.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe residue is purified by preparative HPLC
  3. concentrationThe product fractions are concentrated
  4. additionmixed with 3 ml of 1 N hydrochloric acid
  5. concentrationagain concentrated
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-f55d77b1226c4d48a111a355fcbf2cc1
Source dataset
uspto-grants-2011_10
Patent number
US08030329B2

Reaction notes

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