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

HRID 2362759Notes

Reaction equation

HRID 2362759 reaction equation
[CH2:1]([S:3]([Cl:6])(=[O:5])=[O:4])[CH3:2].Cl.Cl.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([C@@H:25]3[CH:30]4[CH2:31][CH2:32][N:27]([CH2:28][CH2:29]4)[CH2:26]3)=[O:24])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1>CN(C=O)C>[ClH:6].[CH2:1]([S:3]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:23]([C@@H:25]3[CH:30]4[CH2:29][CH2:28][N:27]([CH2:32][CH2:31]4)[CH2:26]3)=[O:24])=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)(=[O:5])=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 67427707(3R)-N-(4'-Aminobiphenyl-4-yl)quinuclidine-3-carboxamide dihydrochloride

Product 1

HCID 11236270(3R)-N-{4'-[(Ethylsulfonyl)amino]biphenyl-4-yl}quinuclidine-3-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

39.1 mg (0.30 mmol) of ethanesulfonyl chloride and 84.8 μl (0.61 mmol) of tiethylamine are added to a solution of 60 mg (0.15 mmol) of ((3R)—N-(4′-aminobiphenyl-4-yl)quinuclidine-3-carboxamide dihydrochloride (Example 7A) in 0.5 ml of DMF. After 18 h at room temperature, the reaction mixture is purified by preparative HPLC. The product fractions are concentrated, mixed with 2 ml of a 1:1 mixture of acetonitrile and 1 N hydrochloric acid, again concentrated and dried under high vacuum. 26 mg (35.2% of theory) of the title compound are obtained. HPLC (Method 1): Rt=3.71 min. MS (ESIpos): m/z=414 (M+H)+.

Workup

  1. customthe reaction mixture is purified by preparative HPLC
  2. concentrationThe product fractions are concentrated
  3. additionmixed with 2 ml of a 1:1 mixture of acetonitrile and 1 N hydrochloric acid
  4. concentrationagain concentrated
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-7b60c8e5716e49e58d7e9fcdbde2e6fc
Source dataset
uspto-grants-2014_04
Patent number
US08691840B2

Reaction notes

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