HCID 86725347, compound → HCID 90272315, compound

HRID 925241Notes

Reaction equation

HRID 925241 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([I:26])[C:14]([O:16][CH2:17][C:18](=O)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][C:8]=2[CH2:7][CH2:6]1)=O>O>[I:26][C:13]1[C:14]2[O:16][CH:17]=[C:18]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:15]=2[C:8]2[CH2:7][CH2:6][NH:5][CH2:11][CH2:10][C:9]=2[CH:12]=1

Participants

3

Reactant 1

HCID 86725347HCID 86725347, compound

Product 1

HCID 90272315HCID 90272315, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Poly phosphoric acid (˜1 ml) was added to a vial containing the product from step (b) (0.255 g, 0.50 mmol) and heated to 90° C. for 20 minutes. Water was added to the reaction mixture and extracted with dichloromethane (3×). The organic layers were washed with saturated sodium bicarbonate, and brine. To the crude material was added 8 ml of methanol, 5 ml of water, and potassium carbonate (˜100 mg). The reaction mixture was allowed to stir at room temperature for 16 hours. The reaction mixture was concentrated and to this was added 2N HCl, and extracted with dichloromethane (3×). Purification by silica-gel chromatography (gradient elution: 0-20% methanol in dichloromethane) gave the sub-title compound as an off white solid (0.034 mg). MS: ESI (positive): 390 (M+H).

Workup

  1. extractionextracted with dichloromethane (3×)
  2. washThe organic layers were washed with saturated sodium bicarbonate, and brine
  3. additionTo the crude material was added 8 ml of methanol, 5 ml of water, and potassium carbonate (˜100 mg)
  4. concentrationThe reaction mixture was concentrated
  5. additionto this was added 2N HCl
  6. extractionextracted with dichloromethane (3×)
  7. customPurification
  8. washby silica-gel chromatography (gradient elution: 0-20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-6c1c4b64c574429a8c219612d4c45c81
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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