Triethylamine → HCID 69005019, compound

HRID 1821420Notes

Reaction equation

[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[CH:21]=[CH:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][N:24]=1)[C:15]([OH:17])=[O:16].C(N(CC)CC)C.[N+:39](C1C=CC=C2C(OC(=O)C=12)=O)([O-:41])=[O:40]>C1(C)C(C)=CC=CC=1>[NH:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23](/[CH:22]=[CH:21]/[C:20]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][C:12]=2[N:3]2[C:2](=[O:1])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][C:9]=3[N+:39]([O-:41])=[O:40])[C:4]2=[O:11])=[N:24]1

Participants

Conditions

Temperature: 140 °C

Procedure

To 3-amino-4-[2-(1H-indazol-3-yl)vinyl]benzoic acid (1.7 g, 6.2 mmol) obtained in Step 2 of Example 276, xylene (55 mL), triethylamine (0.45 mL, 3.1 mmol), 3-nitrophthalic anhydride (1.4 g, 7.4 mmol), molecular sieves 3A (2.0 g) were added, followed by heating at 140° C. for 4 hours. Molecular sieves 3A was filtered off and the reaction mixture was acidified by hydrochloric acid (2 mol/L). The precipitated crystal was collected by filtration to obtain (E)-4-[2-(1H-indazol-3-yl)vinyl]-3-(4-nitro-1,3-dioxo-1,3-dihydroisoindol-2-yl)benzoic acid.

Workup

filtrationMolecular sieves 3A was filtered off
filtrationThe precipitated crystal was collected by filtration

Sources & evidence

ORD record: ord-20870e22fccb4ad1919f090cc96e9620
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605272B2

Reaction notes

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