Phenylmethanesulfonyl chloride → (3R)-N-{4'-[(Benzylsulfonyl)amino]biphenyl-4-yl}quinuclidine-3-carboxamide

HRID 588347노트

반응식

HRID 588347 반응식
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([CH2:33][S:34](Cl)(=[O:36])=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>N1C=CC=CC=1>[CH2:33]([S:34]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17]([C@@H:19]3[CH:24]4[CH2:23][CH2:22][N:21]([CH2:26][CH2:25]4)[CH2:20]3)=[O:18])=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)(=[O:36])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

4

반응물 2

HCID 74740Phenylmethanesulfonyl chlorideHCID 67427707(3R)-N-(4'-Aminobiphenyl-4-yl)quinuclidine-3-carboxamide dihydrochloride

생성물 1

HCID 11375685(3R)-N-{4'-[(Benzylsulfonyl)amino]biphenyl-4-yl}quinuclidine-3-carboxamide

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A solution of 80 mg (0.20 mmol) of ((3R)—N-(4′-aminobiphenyl-4-yl)quinuclidine-3-carboxamide dihydrochloride (Example 7A) and 77.4 mg (0.41 mmol) of phenylmethanesulfonyl 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. 34 mg (32.7% of theory) of the title compound are obtained.

후처리

  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

출처 및 근거

ORD 기록
ord-8f34699617c942ea8f651a0e740f1fdd
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227964B2

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