2,5-Dimethoxytetrahydrofuran → HCID 131728432, compound

HRID 1927453Notes

Reaction equation

HRID 1927453 reaction equation
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)O1.Cl.ClC1C=CN=CC=1.[NH2:18][C:19]1[C:24]2[O:25][C:26]3[CH:35]=[CH:34][C:33]([C:36]([OH:38])=[O:37])=[CH:32][C:27]=3[S:28](=[O:31])(=[O:30])[CH2:29][C:23]=2[CH:22]=[CH:21][CH:20]=1>O1CCOCC1>[O:30]=[S:28]1(=[O:31])[C:27]2[CH:32]=[C:33]([C:36]([OH:38])=[O:37])[CH:34]=[CH:35][C:26]=2[O:25][C:24]2[C:19]([N:18]3[CH:3]=[CH:7][CH:6]=[CH:5]3)=[CH:20][CH:21]=[CH:22][C:23]=2[CH2:29]1

Participants

5

Reactant 3

HCID 790982,5-DimethoxytetrahydrofuranHCID 818524-Chloropyridine hydrochlorideHCID 131728433HCID 131728433, compound

Product 1

HCID 131728432HCID 131728432, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,5-Dimethoxy tetrahydrofuran (0.053 g, 0.40 mmol) and 4-chloropyridine hydrochloride (0.0047 g, 0.03 mmol) were added to a solution of the methyl ester of Example 10k (0.1 g, 0.31 mmol) in dry dioxan (15 mL). The reaction mixture was refluxed with stirring for 1 h, concentrated and extracted with ethyl acetate. The organic layer was washed with water, brine, dried and concentrated to obtain a product which was subsequently hydrolysed as described in the synthesis of Example 11 to obtain the title compound. Yield: 73.7%; 1H NMR (DMSO-d6): δ 5.40 (s, 2H, CH2), 6.40 (s, 2H, pyrrolyl), 6.80 (d, 1H, Ar), 7.10 (s, 2H, pyrrolyl) 7.50-7.70 (m, 3H, Ar), 8.05 (d, 1H, Ar), 8.20 (s, 1H, Ar); MS: m/e (EI+) 355 (M+).

Workup

  1. temperatureThe reaction mixture was refluxed
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. customdried
  6. concentrationconcentrated
  7. customto obtain a product which
  8. customas described in the synthesis of Example 11

Sources & evidence

ORD record
ord-d252e679b3df45a490a0c1e686eff836
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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