HCID 10236495, compound → HCID 10192891, compound

HRID 1794524Notes

Reaction equation

HRID 1794524 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([N+:20]([O-:22])=[O:21])[C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=3)=[CH:8][C:7]=2[CH:19]=1.N1C(=O)CC[C@H]1C(O)=O.Cl>>[OH:17][C:14]1[CH:13]=[CH:12][C:11]([C:9]2[O:10][C:6]3[C:5]([N+:20]([O-:22])=[O:21])=[CH:4][C:3]([OH:2])=[CH:19][C:7]=3[CH:8]=2)=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 10236495HCID 10236495, compoundHCID 67725173Pyr-HCl2×

Product 1

HCID 10192891HCID 10192891, compoundYield 47.3%

Conditions

Temperature
200 °C

Procedure

A mixture of 98 (0.56 g) and Pyr-HCl and heated at 200° C. for 1 h (while occasionally adding more Pyr-HCl). The reaction was allowed to cool and then partitioned between 2 N HCl aq and EtOAc. A small amount of MeOH was added to facilitate the dissolution process. The organic layer was washed with saturated NaHCO3 aq, brine, and dried over MgSO4. Filtration, concentration and trituration of the pdt with CH2Cl2 yielded 0.44 g of the desired pdt which contained some inorganic impurities. The material was then chromatographeid on silica gel (MeOH/CH2Cl2 1:19 to MeOH/CH2Cl2 1:9) to yield 0.24 g of 99: Mp=236–2372° C.; 1H NMR (DMSO-d6) δ 10.06 (br s, 1 H), 7.73 (d, 2 H, J=8.3 Hz), 7.46 (dd, 1 H, J=2.4 Hz, 0.7 Hz), 7.38 (dd, 1 H, J=2.3 Hz, 0.7 Hz), 7.28 (s, 1 H), 6.93 (d, 2 H, J=8.3 Hz); MS 270 (M−H)−.

Workup

  1. temperatureto cool
  2. custompartitioned between 2 N HCl aq and EtOAc
  3. additionA small amount of MeOH was added
  4. washThe organic layer was washed with saturated NaHCO3 aq, brine
  5. dry with materialdried over MgSO4
  6. filtrationFiltration, concentration and trituration of the pdt with CH2Cl2
  7. customyielded 0.44 g of the desired pdt which

Sources & evidence

ORD record
ord-eb92c88743624f39a39d5ea69791a66a
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

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