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Benzenesulfonyl chloride → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-6-[bis(phenylsulfonyl)amino]-1-benzothiophene-2-carboxamide hydrochloride

HRID 335616
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인쇄 미리보기

반응식

HRID 335616 반응식
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C@@H:4]([NH:10][C:11]([C:13]1[S:14][C:15]3[CH:21]=[C:20]([NH2:22])[CH:19]=[CH:18][C:16]=3[CH:17]=1)=[O:12])[CH2:3]2.C(N([CH2:28][CH3:29])CC)C.[C:30]1([S:36]([Cl:39])(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C=O)C.CN(C1C=CN=CC=1)C>[ClH:39].[N:2]12[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9]1)[C@@H:4]([NH:10][C:11]([C:13]1[S:14][C:15]3[CH:21]=[C:20]([N:22]([S:36]([C:29]4[CH:28]=[CH:32][CH:31]=[CH:30][CH:35]=4)(=[O:38])=[O:37])[S:36]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)(=[O:38])=[O:37])[CH:19]=[CH:18][C:16]=3[CH:17]=1)=[O:12])[CH2:3]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 68432473N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-amino-1-benzothiophene-2-carboxamide hydrochloride

생성물 1

HCID 68431062N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-6-[bis(phenylsulfonyl)amino]-1-benzothiophene-2-carboxamide hydrochloride

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine
촉매
HCID 6228Dimethylformamide용매

실험 절차

40 mg (0.11 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-amino-1-benzo-thiophene-2-carboxamide hydrochloride are dissolved in 2 ml of DMF, 6.5 mg (0.05 mmol) of N,N-dimethyl-4-aminopyridine, 59.6 μl (0.43 mmol) of triethylamine and 27.2 μl (0.21 mmol) of benzenesulfonyl chloride are added and the mixture is stirred at room temperature for 16 h. The reaction mixture is purified by preparative HPLC. The product is dissolved in a mixture of 1N aqueous hydrochloric acid and acetonitrile, then again concentrated and dried under high vacuum. 33 mg (50% of theory) of the title compound are obtained.

후처리

  1. customThe reaction mixture is purified by preparative HPLC
  2. dissolutionThe product is dissolved in a mixture of 1N aqueous hydrochloric acid and acetonitrile
  3. concentrationagain concentrated
  4. customdried under high vacuum

출처 및 근거

ORD 기록
ord-195b9c86e01a4bd78ad39e94b1499e1c
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08884017B2

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