Hydrochloric Acid → HCID 51349214, compound

HRID 401093Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10])[CH:5]=O.[C:14]1([C:20](=O)[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[NH2:29][C:30]([NH2:32])=[O:31].Cl>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:32][C:30](=[O:31])[NH:29]2)[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10]

Participants

Conditions

Temperature: 86 °C

Procedure

A mixture of 3-fluoro-4-hydroxy-5-nitrobenzaldehyde (Intermediate 63) (150 mg, 0.81 mmol), 1,2-diphenylethanone (159 mg, 0.81 mmol), urea (145 mg, 2.43 mmol), concentrated hydrochloric acid (0.5 mL) in ethanol (2 mL) was refluxed at 86° C. for 46 hours. After cooling, the mixture was evaporated and the crude product was purified by preparative HPLC to give Compound 127 (136.1 mg, yield 41.4%). 1HNMR (DMSO-d6 400 MHz): δ 11.25 (s, 1H), 8.77 (s, 1H), 7.70 (s, 1H), 7.59 (s, 1H), 7.52-7.49 (m, 1H), 7.27-7.22 (m, 5H), 7.06-6.98 (m, 3H), 6.83 (d, J=6.4 Hz, 2H), 5.27 (d, J=2.4 Hz, 1H); MS (ESI): m/z 406.0 [M+H]+.

Workup

temperatureAfter cooling
customthe mixture was evaporated
customthe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-15b9bf2ad59a4de4b72f643c9417e54e
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741915B2

Reaction notes

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