Dimethylformamide → HCID 136376032, compound

HRID 732085Notes

Reaction equation

HRID 732085 reaction equation
[CH2:1]([N:3]1[C:7]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)=[N:6][N:5]=[C:4]1[S:13][CH2:14][C:15]1[N:19]=[C:18]([C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=2F)[C:23]#[N:24])[O:17][N:16]=1)[CH3:2].[H-].[Na+].CN(C=[O:35])C>>[CH2:1]([N:3]1[C:7]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)=[N:6][N:5]=[C:4]1[S:13][CH2:14][C:15]1[N:19]=[C:18]([C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=2[OH:35])[C:23]#[N:24])[O:17][N:16]=1)[CH3:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 67070774HCID 67070774, compound

Product 1

HCID 136376032HCID 136376032, compoundYield 41%

Procedure

The title compound was prepared using the general procedure of Rogers et al., Tetrahedron Letters (2002) 43: 3585-3587. To a stirring solution of 3-[3-(4-Ethyl-5-furan-2-yl-4H-[1,2,4]triazol-3-ylsulfanylmethyl)-[1,2,4]oxadiazol-5-yl]-4-fluoro-benzonitrile (20 mg, 0.050 mmol), 2-(methylsulfonyl-ethanol) (9.38 mg, 0.075 mmol), and DMF (0.05 M) at 0° C. was added NaH (5.8 mg, 0.150 mmol). Stirred for 20 min and removed the ice bath. Stirred an additional 20 min while warming to room temperature. The reaction mixture was quenched with 1 N HCl solution and partitioned between ethyl acetate and brine. The organic layer was dried (Na2SO4), filtered and concentrated to dryness. The crude organics were purified by flash column chromatography using ethyl acetate followed by 5% methanol in ethyl acetate to give the title compound (8.1 mg, 41%, white solid). 1H NMR (CDCl3), δ (ppm): 8.25 (m, 1H), 7.75 (m, 1H), 7.60 (s, 1H), 7.18 (m, 2H), 6.60 (m, 1H), 4.64 (s, 2H), 4.25 (q, 2H), 1.38 (t, 3H).

Workup

  1. customThe title compound was prepared
  2. customremoved the ice bath
  3. stirringStirred an additional 20 min
  4. customThe reaction mixture was quenched with 1 N HCl solution
  5. custompartitioned between ethyl acetate and brine
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe crude organics were purified by flash column chromatography

Sources & evidence

ORD record
ord-2d3b4be473174d2cbfabeef0799246c9
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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