Trimellitic anhydride → 2-[4-Propylamino-3-[5-(2-benzofuranyl)benzoxazol-2-yl]phenyl]-1,3-dioxo-2,3-dihydro-1h-isoindole-5-carboxylic acid

HRID 722655Notes

Reaction equation

[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[C:12]1[O:13][C:14]2[CH:20]=[CH:19][C:18]([C:21]3[O:22][C:23]4[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=4[CH:25]=3)=[CH:17][C:15]=2[N:16]=1)[CH2:2][CH3:3].[CH:30]1[C:35]([C:36]([OH:38])=[O:37])=[CH:34][C:33]2[C:39]([O:41][C:42](=O)[C:32]=2[CH:31]=1)=[O:40]>>[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:39](=[O:40])[C:33]3[C:32](=[CH:31][CH:30]=[C:35]([C:36]([OH:38])=[O:37])[CH:34]=3)[C:42]2=[O:41])=[CH:7][C:6]=1[C:12]1[O:13][C:14]2[CH:20]=[CH:19][C:18]([C:21]3[O:22][C:23]4[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=4[CH:25]=3)=[CH:17][C:15]=2[N:16]=1)[CH2:2][CH3:3]

Participants

Reactant 2

HCID 11089Trimellitic anhydride

HCID 218846182-(2-Propylamino-5-aminophenyl)-5-(2-benzofuranyl)benzoxazole

Product 1

HCID 218846262-[4-Propylamino-3-[5-(2-benzofuranyl)benzoxazol-2-yl]phenyl]-1,3-dioxo-2,3-dihydro-1h-isoindole-5-carboxylic acid

Procedure

Prepared by the method of Example 1b), from 2-(2-propylamino-5-aminophenyl)-5-(2-benzofuranyl)benzoxazole (50 mg, 0.13 mmol) and 1,2,4-benzenetricarboxylic anhydride (30 mg, 0.13 mmol) the title compound was obtained (40 mg, 55%). 1H NMR (DMSO) δ 8.53(t, 1H), 8.46(dd, 1H), 8.37(d, 2H), 8.18(d, 1H), 8.12(d, 1H), 8.05(dd, 1H), 7.93(d, 1H), 7.72(m, 2H), 7.60(s, 1H), 7.54(dd, 1H), 7.36(m, 2H), 7.10(d, 1H), 3.44(m, 2H), 1.84(m, 2H), 1.15(t, 3H). MS 556 m/z (M−H)−.

Sources & evidence

ORD record: ord-b6fd6fde2549425c9cbcfb81e39823df
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138425B2

Reaction notes

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