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

HRID 588345Notes

Reaction equation

HRID 588345 reaction equation
[CH2:1]([S:3]([Cl:6])(=[O:5])=[O:4])[CH3:2].C(N(CC)CC)C.Cl.Cl.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30]([C@@H:32]3[CH:37]4[CH2:38][CH2:39][N:34]([CH2:35][CH2:36]4)[CH2:33]3)=[O:31])=[CH:25][CH:24]=2)=[CH:19][CH:18]=1>CN(C=O)C>[ClH:6].[CH2:1]([S:3]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:24]=[CH:25][C:26]([NH:29][C:30]([C@@H:32]3[CH:37]4[CH2:36][CH2:35][N:34]([CH2:39][CH2:38]4)[CH2:33]3)=[O:31])=[CH:27][CH:28]=2)=[CH:19][CH:18]=1)(=[O:5])=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 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 triethylamine 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.

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-49e96b9f26e04bc89384d2b04f52b922
Source dataset
uspto-grants-2016_01
Patent number
US09227964B2

Reaction notes

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