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

HRID 722662Notes

Reaction equation

HRID 722662 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH3:28])[CH:22]=4)=[CH:17][C:15]=3[N:16]=2)[C:5]([NH:8][CH2:9][CH2:10][CH3:11])=[CH:6][CH:7]=1.[CH:29]1[C:34]([C:35]([OH:37])=[O:36])=[CH:33][C:32]2[C:38]([O:40][C:41](=O)[C:31]=2[CH:30]=1)=[O:39]>C(O)(=O)C>[CH2:9]([NH:8][C:5]1[C:4]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH3:28])[CH:22]=4)=[CH:17][C:15]=3[N:16]=2)=[CH:3][C:2]([N:1]2[C:38](=[O:39])[C:32]3[C:31](=[CH:30][CH:29]=[C:34]([C:35]([OH:37])=[O:36])[CH:33]=3)[C:41]2=[O:40])=[CH:7][CH:6]=1)[CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 11089Trimellitic anhydrideHCID 218844722-(3-Amino-6-propylaminophenyl)-5-(3-methyl-4-chlorophenyl)benzoxazole

Product 1

HCID 218845332-[4-Propylamino-5-[5-(3-methyl-4-chlorophenyl)benzoxazol-2-yl]phenyl]-1,3-dioxo-2,3-dihydro-1h-isoindole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared by the method of Example 15f), from 2-(3-amino-6-propylaminophenyl)-5-(3-methyl-4-chlorophenyl)benzoxazole (94 mg, 0.24 mmol) and 1,2,4-benzenetricarboxylic anhydride (45.6 mg, 0.24 mmol) in acetic acid (10 ml) the title compound was obtained (109 mg, 81%). 1H NMR (DMSO) δ 13.79(s, 1H), 8.49(t, 1H), 8.42(dd, 1H), 8.31(s, 1H), 8.12(d, 1H), 8.07(m, 2H), 7.83(d, 1H), 7.80(d, 1H), 7.71(dd, 1H), 7.61(dd, 1H), 7.48(m, 2H), 7.03(d, 1H), 3.38(m, 2H), 2.42(s, 3H), 1.76(m, 2H), 1.08(t, 3H). MS 566.2 m/z (M+H)+.

Sources & evidence

ORD record
ord-830170ccdc744394a6954fd84a591aad
Source dataset
uspto-grants-2006_11
Patent number
US07138425B2

Reaction notes

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