Tetrahydrofuran → HCID 69385147, compound

HRID 916852Notes

Reaction equation

HRID 916852 reaction equation
[CH3:1][C:2]1([CH3:37])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@@H:12]([OH:36])[CH2:13][NH:14][CH2:15][CH2:16][C:17]3[CH:35]=[CH:34][C:20]([O:21][CH2:22][CH2:23][O:24][CH2:25][C:26]4[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=4)[C:29]#[N:30])=[CH:19][CH:18]=3)=[CH:11][C:5]=2[CH2:4][O:3]1.[O:38]1CCCC1>>[CH3:1][C:2]1([CH3:37])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@@H:12]([OH:36])[CH2:13][NH:14][CH2:15][CH2:16][C:17]3[CH:35]=[CH:34][C:20]([O:21][CH2:22][CH2:23][O:24][CH2:25][C:26]4[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=4)[C:29]([NH2:30])=[O:38])=[CH:19][CH:18]=3)=[CH:11][C:5]=2[CH2:4][O:3]1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 69386822HCID 69386822, compound

Product 1

HCID 69385147HCID 69385147, compound

Conditions

Temperature
70 °C

Procedure

A solution of 3-({2-[4-(2-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}ethyl)phenoxy]ethoxy}methyl)benzonitrile (4.6 g) in tetrahydrofuran (70 ml) was treated with potassium trimethylsilanoate (9.32 g) and heated at 70° C. for 71 h. The reaction mixture was concentrated in vacuo and partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate and the combined organic phase washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography (SPE, eluted with a gradient between dichloromethane and 10% methanol in dichloromethane) to give the title compound (1.01 g). LCMS RT=2.42 min.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned between ethyl acetate and water
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organic phase washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography (SPE
  8. washeluted with a gradient between dichloromethane and 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-5253e044a7b94f1aadc6dc8829c1116f
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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