HCID 10236495, compound → HCID 10192891, compound

HRID 1836027Notes

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

Reactant 2

HCID 10236495HCID 10236495, compound

HCID 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 chromatographed on silica gel (MeOH/CH2Cl2 1:19 to MeOH/CH2Cl2 1:9) to yield 0.24 g of 99: Mp=236-237° 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

temperatureto cool
custompartitioned between 2 N HCl aq and EtOAc
additionA small amount of MeOH was added
washThe organic layer was washed with saturated NaHCO3 aq, brine
dry with materialdried over MgSO4
filtrationFiltration, concentration and trituration of the pdt with CH2Cl2
customyielded 0.44 g of the desired pdt which
customThe material was then chromatographed on silica gel (MeOH/CH2Cl2 1:19 to MeOH/CH2Cl2 1:9)

Sources & evidence

ORD record: ord-2f6acff1864147b5b243a3346022c763
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06774248B2

Reaction notes

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