Hydrochloric Acid → HCID 51348951, compound

HRID 401081Notes

Reaction equation

[CH:1]([C:3]1[CH:4]=[C:5]([N+:13]([O-:15])=[O:14])[C:6]([OH:12])=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9])=O.[C:16]1([C:22](=O)[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH2:31][C:32]([NH2:34])=[O:33].Cl>C(O)C>[OH:12][C:6]1[C:5]([N+:13]([O-:15])=[O:14])=[CH:4][C:3]([CH:1]2[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:34][C:32](=[O:33])[NH:31]2)=[CH:11][C:7]=1[C:8]([OH:10])=[O:9]

Participants

Conditions

Temperature: 78 °C

Procedure

A mixture of 5-formyl-2-hydroxy-3-nitrobenzoic acid (Intermediate 55) (200 mg, 0.95 mmol), 1,2-diphenylethanone (185.8 mg, 0.95 mmol), urea (170.5 mg, 2.84 mmol), concentrated hydrochloric acid solution (0.3 mL) in ethanol (2 mL) was refluxed at 78° C. for 33 h. The reaction mixture was evaporated in vacuo, and purified by preparative HPLC to give Compound 110 (75.7 mg, yield 18.5%). 1H NMR (DMSO-D6, 400 MHZ): δ 8.78 (s, 1H), 8.15 (d, J=2.0 Hz, 1H), 8.09 (d, J=2.4 Hz, 1H), 7.60 (s, 1H), 7.26-7.19 (m, 5H), 7.04-6.99 (m, 3H), 6.81 (d, J=6.4 Hz, 2H), 5.27 (d, J=2.8 Hz, 1H); MS (ESI): m/z 432.1 [M+H]+.

Workup

customThe reaction mixture was evaporated in vacuo
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-5a073ff0290e4190bf6349a04e47d6d8
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741915B2

Reaction notes

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