Potassium Carbonate → 4-{[4-(4-Hydroxy-phenylsulfanyl)-butyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile

HRID 19906

반응식

HRID 19906 반응식
C(=O)([O-])[O-].[K+].[K+].Br[CH:8]([CH2:24][CH3:25])[CH2:9][N:10]([N:19]1[CH:23]=[N:22][N:21]=[CH:20]1)[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1.[OH:26][C:27]1[CH:32]=[CH:31][C:30]([SH:33])=[CH:29][CH:28]=1>CN(C=O)C.C(OCC)(=O)C>[OH:26][C:27]1[CH:32]=[CH:31][C:30]([S:33][CH2:25][CH2:24][CH2:8][CH2:9][N:10]([N:19]2[CH:23]=[N:22][N:21]=[CH:20]2)[C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)=[CH:29][CH:28]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 2401474-MercaptophenolHCID 219768514-[(2-Bromo-butyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile

생성물 1

HCID 219768574-{[4-(4-Hydroxy-phenylsulfanyl)-butyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Potassium carbonate (500 mg) was added to a solution of 4-[(2-bromo-butyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile (CAB03001, 384 mg, 1.2 mmol) and 4-hydroxythiophenol (227 mg, 1.8 mmol) in DMF (20 mL). The mixture was stiffed for 18 hours at r.t., diluted with ethyl acetate (100 mL) and extracted with water (two times 30 mL) and brine (30 mL). The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography (eluent: ethyl acetate, Rf: 0.30). The resulting oil was dissolved in a small amount of ethyl acetate and the product was precipitated by addition of hexane. Yield: 289 mg (66%). 1H-NMR (400 MHz, d6-DMSO) δ=1.48-1.64 (m, 4H) 2.81 (t, J=6.6 Hz, 2H), 3.81 (t, J=6.8 Hz, 2H), 6.62 (d, J=9.0 Hz, 2H), 6.72 (d, J=8.6 Hz, 2H), 7.19 (d, J=9.0 Hz, 2H), 7.72 (d, J=9.0, 2H), 8.94 (s, 2H), 9.56 (s, 1H, —OH). LRMS (FAB+): 366.1 (100, [M+H]+).

후처리

  1. extractionextracted with water (two times 30 mL) and brine (30 mL)
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography (eluent: ethyl acetate, Rf: 0.30)
  5. dissolutionThe resulting oil was dissolved in a small amount of ethyl acetate
  6. customthe product was precipitated by addition of hexane

출처 및 근거

ORD 기록
ord-4bebb1482b4e44bf8af570d5cc5190fb
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745472B2

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