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Hydrochloric Acid → 2-Hydroxy-3-[5-(piperazine-1-sulfonyl)pyridin-2-yl]-1H-indole-6-carbonitrile hydrochloride

HRID 2245559
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HRID 2245559 반응식
[H-].[Na+].[O:3]=[C:4]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([C:13]#[N:14])=[CH:9][CH:10]=2)[NH:5]1.[Cl:15][C:16]1[N:21]=[CH:20][C:19]([S:22]([N:25]2[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]2)(=[O:24])=[O:23])=[CH:18][CH:17]=1.Cl.C(OCC)C>CN1CCCC1=O.CO>[ClH:15].[OH:3][C:4]1[NH:5][C:6]2[C:11]([C:12]=1[C:16]1[CH:17]=[CH:18][C:19]([S:22]([N:25]3[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]3)(=[O:24])=[O:23])=[CH:20][N:21]=1)=[CH:10][CH:9]=[C:8]([C:13]#[N:14])[CH:7]=2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 27733482-Oxindole-6-carbonitrileHCID 11739940Tert-butyl 4-(6-chloropyridin-3-ylsulfonyl)piperazine-1-carboxylate

생성물 1

HCID 1354316282-Hydroxy-3-[5-(piperazine-1-sulfonyl)pyridin-2-yl]-1H-indole-6-carbonitrile hydrochloride
수율 99.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

To a suspension of sodium hydride (97%, 0.024 g, 1.0 mmol) in 1-methyl-2-pyrrolidinone (2 mL) was added 2-oxoindoline-6-carbonitrile (0.119 g, 0.75 mmol). The formed mixture was stirred for 5 min at room temperature and tert-butyl 4-[(6-chloropyridin-3-yl)sulfonyl]piperazine-1-carboxylate (0.181 g, 0.5 mmol) was added. The resulting reaction mixture was set under an N2 atmosphere and stirred for 1 h at 90° C. Methanol (0.5 mL) was added to the mixture and the solvents were removed in vacuo. The crude product was dissolved in methanol (5 mL) and HCl in diethyl ether (4 M, 2.5 mL, 10 mmol) was added followed by reflux for 3 h. From the cooled solution the formed yellow precipitate was collected by filtration and dried to give 0.209 g (92% yield) of the title compound: 1H NMR (DMSO-d6, 400 MHz) δ 11.08 (s, 1H), 9.10 (br s, 2H), 8.67 (s, 1H), 7.89 (s, 2H), 7.78 (d, J=8.0 Hz, 1H), 7.44 (dd, J=8.0, 1.2 Hz, 1H), 7.28 (d, J=1.2 Hz, 1H) 3.31 (br s, 4H), 3.25 (br s, 4H); MS (EI) m/z 384 (M++1).

후처리

  1. customThe resulting reaction mixture
  2. stirringstirred for 1 h at 90° C
  3. customthe solvents were removed in vacuo
  4. dissolutionThe crude product was dissolved in methanol (5 mL)
  5. temperatureby reflux for 3 h
  6. filtrationFrom the cooled solution the formed yellow precipitate was collected by filtration
  7. customdried

출처 및 근거

ORD 기록
ord-a242f4906fdb467fb13e747373597e88
출처 데이터셋
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07683067B2

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