Cesium carbonate → HCID 135405882, compound

HRID 2224773Notes

Reaction equation

HRID 2224773 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]([C:14]1[C:23](=[O:24])[C:22]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:25][CH2:26][CH2:27][CH3:28])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]=1[OH:33])=O)(=[O:4])=[O:3].C(=O)([O-])[O-].[Cs+].[Cs+]>N1C=CC=CC=1>[CH2:25]([C:22]1([CH2:29][CH2:30][CH2:31][CH3:32])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([OH:33])=[C:14]([C:12]2[NH:11][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[S:2](=[O:4])(=[O:3])[N:1]=2)[C:23]1=[O:24])[CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 68872527HCID 68872527, compound

Product 1

HCID 135405882HCID 135405882, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

A solution of the product of Example 4G (298 mg, 0.63 mmol) and cesium carbonate (123 mg, 0.38 mmol) in pyridine (6 mL) was stirred at 140° C. for 18 hours, cooled to 25° C. and the pyridine removed by short path distillation under high vacuum (50° C./0.3 mm Hg). A suspension of the residue in ethyl acetate was treated with saturated ammonium chloride solution. The organic layer was washed with water and saturated sodium chloride solution, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with ethyl acetate in hexane to afford the title compound (157 mg, 55%). 1H NMR (300 MHz, CDCl3): δ 16.71 (d, J=3.68 Hz, 1 H), 14.39 (s, 1 H), 14.24 (s, 1 H), 8.28 (d, J=8.09 Hz, 1 H), 7.99 (d, J=8.09 Hz, 1 H), 7.66 (m, 1 H), 7.46 (m, 1 H), 7.31 (m, 6 H), 2.30 (m, 2 H), 1.92 (m, 2 H), 1.16 (m, 3 H), 0.88 (m, 2 H), 0.62 (m, 7 H).

Workup

  1. customthe pyridine removed by short path distillation under high vacuum (50° C./0.3 mm Hg)
  2. additionA suspension of the residue in ethyl acetate
  3. additionwas treated with saturated ammonium chloride solution
  4. washThe organic layer was washed with water and saturated sodium chloride solution
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel
  9. washeluting with ethyl acetate in hexane

Sources & evidence

ORD record
ord-caf59b3826fd4972a6ffa17ec33c77ab
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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