Phthalic Anhydride → HCID 178487812, compound

HRID 1422962Notes

Reaction equation

HRID 1422962 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH3:12][O:13][C:14]1[N:15]=[C:16]2[C:25](=[CH:26][CH:27]=1)[N:24]=[CH:23][C:22]1[O:21][CH2:20][CH:19]([C@H:28]3[CH2:33][CH2:32][C@H:31]([NH2:34])[CH2:30][CH2:29]3)[NH:18][C:17]2=1>N1C=CC=CC=1>[CH3:12][O:13][C:14]1[N:15]=[C:16]2[C:25](=[CH:26][CH:27]=1)[N:24]=[CH:23][C:22]1[O:21][CH2:20][CH:19]([C@H:28]3[CH2:33][CH2:32][C@H:31]([N:34]4[C:1](=[O:11])[C:2]5[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=5)[C:4]4=[O:6])[CH2:30][CH2:29]3)[NH:18][C:17]2=1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 178487813HCID 178487813, compound

Product 1

HCID 178487812HCID 178487812, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Phthalic anhydride (200 mg, 1.34 mmol, 2.53 eq) is added at room temperature to a stirred solution of trans-4-(6-methoxy-3,4-dihydro-2H-1-oxa-4,5,9-triaza-phenanthren-3-yl)-cyclohexylamine (200 mg, 0.53 mmol, 1.0 eq) in pyridine (4 mL). The reaction mixture is heated to reflux for 3 hours, pyridine is then removed and acetic anhydride (1 mL) is added. The resulting mixture is heated to reflux for 2 hours, then extracted with ethyl acetate (3×10 mL) and water (5 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford 2-[trans-4-(6-methoxy-3,4-dihydro-2H-1-oxa-4,5,9-triaza-phenanthren-3-yl)-cyclohexyl]-isoindole-1,3-dione as a light brown semisolid (190 mg, 69% yield).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 3 hours
  3. custompyridine is then removed
  4. additionacetic anhydride (1 mL) is added
  5. temperatureThe resulting mixture is heated
  6. temperatureto reflux for 2 hours
  7. extractionextracted with ethyl acetate (3×10 mL) and water (5 mL)
  8. dry with materialThe combined organic layers are dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-18ea72b6248b4c24aa1307d81c90cb90
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

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