4-tert-Butylphthalic anhydride → HCID 15543027, compound

HRID 2301825Notes

Reaction equation

HRID 2301825 reaction equation
[NH2:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[N:12][N:13]2C(OC(C)(C)C)=O)=[CH:9][CH:8]=1)=[O:5].[C:27]([C:31]1[CH:32]=[C:33]2[C:38](=O)[O:37][C:35](=[O:36])[C:34]2=[CH:40][CH:41]=1)([CH3:30])([CH3:29])[CH3:28]>C1COCC1.C(OCC)C>[NH:13]1[C:14]2[C:10](=[CH:9][CH:8]=[C:7]([NH:6][C:4](=[O:5])[C:3]3[CH:23]=[CH:24][CH:25]=[CH:26][C:2]=3[N:1]3[C:38](=[O:37])[C:33]4[C:34](=[CH:40][CH:41]=[C:31]([C:27]([CH3:29])([CH3:28])[CH3:30])[CH:32]=4)[C:35]3=[O:36])[CH:15]=2)[CH:11]=[N:12]1

Participants

5

Reactant 2

HCID 1229304-tert-Butylphthalic anhydrideHCID 15543039HCID 15543039, compound

Product 1

HCID 15543027HCID 15543027, compoundYield 16.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 2-amino-N-(1-Boc-6-indazolyl)benzamide (1 g, 2.8 mmol) in THF (30 mL) was added 4-t-butylphthalic anhydride (1.2 g, 5.9 mmol) and the solution was heated to reflux. After 72 h, the vessel was cooled and the volume was reduced to about 10 mL in vacuo. The mixture was diluted with diethyl ether (20 mL) and after sonication, a white solid was collected. This solid was processed by methods substatially equivalent to those described in Example 2-F to give 200 mg of N-(6-indazolyl)-2-(5-t-butyl-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)benzamide.

Workup

  1. temperaturethe solution was heated to reflux
  2. temperaturethe vessel was cooled
  3. customafter sonication
  4. customa white solid was collected

Sources & evidence

ORD record
ord-6d49e21c1e7d4c6294bc9dcd6f7aafda
Source dataset
uspto-grants-2002_12
Patent number
US06500851B2

Reaction notes

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