Tetrahydrofuran → HCID 67007803, compound

HRID 1946601Notes

Reaction equation

HRID 1946601 reaction equation
Br[C:2]1[S:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:6]=1.[Cl-].[F:13][C:14]([F:29])([F:28])[C:15]1[CH:16]=[C:17]([N:21]2[CH2:26][C@@H:25]3[CH2:27][C@H:22]2[CH2:23][NH2+:24]3)[CH:18]=[CH:19][CH:20]=1.C(N(CC)CC)C.C1COCC1>O1CCOCC1>[F:29][C:14]([F:13])([F:28])[C:15]1[CH:16]=[C:17]([N:21]2[CH2:26][C@@H:25]3[CH2:27][C@H:22]2[CH2:23][N:24]3[C:2]2[S:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:6]=2)[CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 3614103Ethyl 2-bromothiazole-5-carboxylateHCID 67006616HCID 67006616, compound

Product 1

HCID 67007803HCID 67007803, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of ethyl 2-bromothiazole-5-carboxylate (0.125 mL, 0.834 mmol), title compound 216 (425 mg, 1.525 mmol), and triethylamine (0.465 mL, 3.34 mmol) in dioxane (1.525 mL) was sonicated for 1 h. More THF (2 mL) was added and the mixture was sonicated for another 2 h. The mixture was partitioned between water and ethyl acetate and the organic layer was washed with water (×2) then with brine. The organic extract was dried (magnesium sulfate) and solvent evaporated. The residue was purified via ISCO (0-50% Hex/EtOAc; 40 g silica gel column) to obtain title compound 217 (316 mg, 95%) as a white foam. LRMS: (calc) 397.11 (found) 398.1 (MH)+.

Workup

  1. customwas sonicated for 1 h
  2. customthe mixture was sonicated for another 2 h
  3. customThe mixture was partitioned between water and ethyl acetate
  4. washthe organic layer was washed with water (×2)
  5. extractionThe organic extract
  6. dry with materialwas dried (magnesium sulfate) and solvent
  7. customevaporated
  8. customThe residue was purified via ISCO (0-50% Hex/EtOAc; 40 g silica gel column)

Sources & evidence

ORD record
ord-25ac18545fd2403caaaf6a2cce2cca83
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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