HCID 10172455, compound → HCID 10236546, compound

HRID 1836029Notes

Reaction equation

HRID 1836029 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, 1H, 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-ca415f6d2bda41a28368bef905a713ff
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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