HCID 10172455, compound → HCID 10236546, compound

HRID 1794526Notes

Reaction equation

HRID 1794526 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[C:10](=[O:22])[CH2:11][C:12]1[CH:17]=[C:16]([O:18]C)[CH:15]=[CH:14][C:13]=1OC.N1C(=O)CC[C@H]1C(O)=O.Cl>>[Br:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:10]1[O:22][C:13]2[CH:14]=[CH:15][C:16]([OH:18])=[CH:17][C:12]=2[CH:11]=1

Participants

3

Reactant 2

HCID 10172455HCID 10172455, compoundHCID 67725173Pyr-HCl

Product 1

HCID 10236546HCID 10236546, compound

Procedure

Compound 101 (1.25 g, 3.4 mmol) was heated at 200° C. with a large excess of Pyr-HCl and followed by TLC for reaction completion (approx 30 min to 1 h). The reaction mixture was allowed to cool to rt and then partitioned between 2 N HCl aq and EtOAc. The organic layer was washed with saturated NaHCO3 aq, brine, and then dried over MgSO4. After filtering, the reaction mixture was concentrated and chromatographed on silica gel (1:1 EtOAc/hexanes) to yield 0.96 g of the desired pdt: Mp=195° C.; 1H NMR (DMSO-d6) δ 10.33 (br s, 1 H), 9.23 (br s, 1 H), 7.70 (d, 1 H, J=8.6 Hz); 7.37 (d, 1 H, J=8.8 Hz), 7.21 (s, 1 H), 7.16 (d, 1 H, J=2.4 Hz), 6.97 (d, 1 H, J=2.4 Hz), 6.92 (dd, 1 H, J=8.7 Hz, 2.4 Hz), 6.75 (dd, 1 H, J=8.8 Hz, 2.4 Hz); MS 303 (M−H)−.

Workup

  1. customfollowed by TLC for reaction completion (approx 30 min to 1 h)
  2. custompartitioned between 2 N HCl aq and EtOAc
  3. washThe organic layer was washed with saturated NaHCO3 aq, brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtering
  6. concentrationthe reaction mixture was concentrated
  7. customchromatographed on silica gel (1:1 EtOAc/hexanes)
  8. customto yield 0.96 g of the desired pdt

Sources & evidence

ORD record
ord-f8a5b56e47884bd98b53ad3a2ac6fdd5
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

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