1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 25234167, compound

HRID 2421853Notes

Reaction equation

HRID 2421853 reaction equation
[C:1]([NH:4][NH:5][C:6]([C:8]1[CH:26]=[CH:25][C:11]2[S:12][CH2:13][CH2:14][N:15]([S:16]([C:19]3[N:20]=[CH:21][N:22]([CH3:24])[CH:23]=3)(=[O:18])=[O:17])[C:10]=2[CH:9]=1)=[O:7])(=O)[CH3:2].C1CCN2C(=NCCC2)CC1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[CH3:2][C:1]1[O:7][C:6]([C:8]2[CH:26]=[CH:25][C:11]3[S:12][CH2:13][CH2:14][N:15]([S:16]([C:19]4[N:20]=[CH:21][N:22]([CH3:24])[CH:23]=4)(=[O:17])=[O:18])[C:10]=3[CH:9]=2)=[N:5][N:4]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 67243292HCID 67243292, compound

Product 1

HCID 25234167HCID 25234167, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N′-acetyl-4-(1-methyl-1H-imidazol-4-ylsulfonyl)-3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carbohydrazide (25 mg, 63 μmol) in THF (1 mL) was added DBU (14 mg, 95 μmol) and Burgess reagent (75 mg, 316 μmol). The reaction vial was capped subjected to microwave irradiation (150° C., 10 min). LCMS analysis of the reaction mixture indicated that the starting material had been consumed. The reaction was diluted with saturated aqueous NaHCO3 (1 mL) and EtOAc (2 mL). The organic layer was removed and the aqueous layer was extracted with EtOAc (2 mL). The organic layers were combined, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography with a gradient elution of hexanes with 10-60% EtOAc to provide 2-methyl-5-(4-(1-methyl-1H-imidazol-4-ylsulfonyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-6-yl)-1,3,4-oxadiazole (16 mg, 42 μmol, 67% yield). LCMS (+ESI) m/z=377.8 [M+H]+; 1H-NMR (CDCl3) δ 8.05 (m, 2H), 7.9 (d, 2H), 7.8 (d, 2H), 7.4-7.5 (m, 3H), 7.25 (d, 1H), 7.1 (dd, 1H), 6.75 (d, 1H), 3.5 (t, 2H), 3.1 (t, 2H).

Workup

  1. customThe reaction vial was capped
  2. customsubjected to microwave irradiation (150° C., 10 min)
  3. customhad been consumed
  4. additionThe reaction was diluted with saturated aqueous NaHCO3 (1 mL) and EtOAc (2 mL)
  5. customThe organic layer was removed
  6. extractionthe aqueous layer was extracted with EtOAc (2 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash column chromatography with a gradient elution of hexanes with 10-60% EtOAc

Sources & evidence

ORD record
ord-d33a638d51a04ace9345427085a9d4d4
Source dataset
uspto-grants-2011_06
Patent number
US07960376B2

Reaction notes

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