4-Amino-2-methoxy-3-[(1-methyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-benzoic Acid Methyl Ester → HCID 178497318, compound

HRID 39663Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH:11][C:12]([C:14]2[N:15]([CH3:22])[CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=2)=O)[C:5]=1[O:23][CH3:24]>C(O)(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]=[C:12]([C:14]3[N:15]([CH3:22])[CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=3)[NH:11][C:6]=2[C:5]=1[O:23][CH3:24])=[O:25]

Participants

Conditions

Temperature: 90 °C

Procedure

The aforementioned mixture of amides 14a/14b (500 mg, 1.43 mmol) was suspended in glacial acetic acid (8 mL) and heated to 90° C. for 7 h. Most of the solvent was evaporated, and the yellow residue was suspended in Et2O. After being vigorously stirred for 20 min, the precipitate was filtered and washed with Et2O. Drying under hv gave 404 mg (85%) of 15 as a beige solid. Data of 15: Rf 0.80 (hexane/EtOAc 1:5). 1H NMR (300 MHz, DMSOd6): δ 3.76 (s, 3H), 4.14 (s, 3H), 4.34 (s, 3H), 7.14-7.17 (m, 1H), 7.48-7.55 (m, 3H), 8.25 (s, 1H). MS (ESI): m/z (rel intensity) 331 (98).

Workup

customMost of the solvent was evaporated
filtrationthe precipitate was filtered
washwashed with Et2O
customDrying under hv

Sources & evidence

ORD record: ord-470fd18e4c004da9bf043eb5c0be01eb
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524899B2

Reaction notes

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