Ethyl Acetate → 4-{[2-(3-Hydroxy-phenylsulfanyl)-ethyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile

HRID 1685664

反応式

HRID 1685664 の反応式
Br[CH2:2][CH2:3][N:4]([N:13]1[CH:17]=[N:16][N:15]=[CH:14]1)[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1.[O:18]([C:26]1[CH:27]=[C:28]([SH:32])[CH:29]=[CH:30][CH:31]=1)[Si](C(C)(C)C)(C)C.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C.O>[OH:18][C:26]1[CH:27]=[C:28]([S:32][CH2:2][CH2:3][N:4]([N:13]2[CH:17]=[N:16][N:15]=[CH:14]2)[C:5]2[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=2)[CH:29]=[CH:30][CH:31]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 219768444-[(2-Bromo-ethyl)-[1,2,4]triazol-4-yl-amino]-benzonitrileHCID 219768683-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]benzenethiol

生成物 1

HCID 219769104-{[2-(3-Hydroxy-phenylsulfanyl)-ethyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4-[(2-Bromo-ethyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile (CAB02148=CAB03031, 146 mg, 0.50 mmol), 3-(tert-butyl-dimethylsiloxy)-thiophenol (240 mg, 1.0 mmol) and potassium carbonate (276 mg, 2.0 mmol) in DMF (10 ml) was stirred for 48 hours at room temperature. The mixture was transferred into a separation funnel and ethyl acetate (50 ml) and water (50 ml) were added. The organic layer was separated, washed with brine (30 ml), dried over sodium sulphate and concentrated under reduced pressure. The residue was crystallised from methanol. Yield: 93 mg (55%) colourless crystals (STX512). 1H-NMR (400 MHz, d6-DMSO) δ=3.14 (t, J=7.0 Hz, 2H), 4.02 (t, J=7.0 Hz, 2H), 6.53 (d, J=9.0 Hz, 2H), 6.62 (ddd, J=7.8, 2.0, 0.8 Hz, 1H), 6.70-6.72 (m, 2H), 7.10 (dd, J=7.8, 7.8, 1H), 7.70 (d, J=9.0 Hz, 2H), 8.94 (s, 2H), 9.60 (s, 1H, —OH). 13C-NMR (100 MHz, d6-DMSO) δ=29.53 52.46, 102.38, 112.86, 113.57, 115.36, 119.00, 130.11, 133.94, 135.82, 143.50, 150.71, 157.90, 169.59. LRMS (FAB+): 338.2 (100, [M+H]+). C17H15N5OS (337.4) Calculated: C, 60.52% H, 4.48% N, 20.76%, Found: C, 60.6% H, 4.53% N, 20.8%.

後処理

  1. customThe mixture was transferred into a separation funnel
  2. customThe organic layer was separated
  3. washwashed with brine (30 ml)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallised from methanol

出典と根拠

ORDレコード
ord-5276d23471da4115844b9054ec50d83e
出典データセット
uspto-grants-2012_04
特許番号
US08148415B2

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