Hydrochloric Acid → HCID 56961404, compound

HRID 924829Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH3:12])[C:9]=1[OH:10])[CH:5]=O.[C:13]1([C:19](=O)[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH2:28][C:29]([NH2:31])=[O:30].Cl>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:31][C:29](=[O:30])[NH:28]2)[CH:7]=[C:8]([O:11][CH3:12])[C:9]=1[OH:10]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-fluoro-4-hydroxy-5-methoxybenzaldehyde (50 mg, 0.294 mmol), 1,2-diphenylethanone (57.7 mg, 0.294 mmol), urea (52.9 mg, 0.882 mmol), and concentrated HCl solution (0.5 mL) in ethanol (2 mL) was refluxed at 80° C. for 52 h. The reaction mixture was evaporated under reduced pressure, and the residue was purified by preparative HPLC to give Compound 68 (32.1 mg, yield 28%). 1HNMR (DMSO-d6 400 MHZ): δ 9.25 (s, 1H), 8.70 (s, 1H), 7.49 (s, 1H), 7.32-7.26 (m, 5H), 7.11-7.05 (m, 3H), 6.88 (d, J=1.6 Hz, 2H), 6.86-6.79 (m, 2H), 5.11 (d, J=2.8 Hz, 1H), 3.79 (s, 3H); MS (ESI): m/z 391.0 [M+H]+.

Workup

customThe reaction mixture was evaporated under reduced pressure
customthe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-3cdcd9226db5420b8cc3b058df7b7e22
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09283229B2

Reaction notes

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