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2-Chloro-3-isothiocyanatopyridine → Methyl 4-(5-bromo-2-(thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-ylthio)benzoate hydrochloride

HRID 335187
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HRID 335187 반응식
[NH2:1][C:2]1[C:7]([S:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[CH:6][C:5]([Br:19])=[CH:4][N:3]=1.[Cl:20][C:21]1[C:26]([N:27]=[C:28]=[S:29])=[CH:25][CH:24]=[CH:23][N:22]=1>CN(C=O)C.ClCCl>[ClH:20].[Br:19][C:5]1[CH:6]=[C:7]([S:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[C:2]([NH:1][C:28]2[S:29][C:21]3[C:26]([N:27]=2)=[CH:25][CH:24]=[CH:23][N:22]=3)=[N:3][CH:4]=1
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참가 물질

5

반응물 2

HCID 128680882-Chloro-3-isothiocyanatopyridineHCID 66994425Methyl 4-(2-amino-5-bromopyridin-3-ylthio)benzoate

생성물 1

HCID 86631508Methyl 4-(5-bromo-2-(thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-ylthio)benzoate hydrochloride수율 41.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

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온도
80 °C

실험 절차

Added methyl 4-(2-amino-5-bromopyridin-3-ylthio)benzoate (1.00 g, 2.95 mmol) to a mixture of 2-chloro-3-isothiocyanatopyridine (0.503 g, 2.95 mmol) in DMF (4 mL). Stirred at 80° C. for an hour, then at 110° C. for 2 hours. Cooled, diluted with dichloromethane (8 mL), filtered, washed with dichloromethane, and dried to afford the title compound (0.625 g, 41.6% yield). 1H NMR (ds-DMSO) δ 3.84 (s, 3H), 7.40 (dd, 1H), 7.45 (d, 2H), 7.72 (d, 1H), 7.79 (bs, 1H), 7.96 (d, 2H), 8.34 (d, 1H), 8.56 (s, 1H).

후처리

  1. temperatureCooled
  2. filtrationfiltered
  3. washwashed with dichloromethane
  4. customdried

출처 및 근거

ORD 기록
ord-2dba8e12e3d440778c728183574e5a56
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08883828B2

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