Hydrochloric Acid → HCID 66826233, compound

HRID 924883Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:17]([O:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([N+:29]([O-:31])=[O:30])[C:27]=1[OH:28])[CH:23]=O)[CH3:18].[NH2:32][C:33]([NH2:35])=[O:34].Cl>C(O)C>[CH2:17]([O:19][C:20]1[CH:21]=[C:22]([CH:23]2[C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=3)[NH:35][C:33](=[O:34])[NH:32]2)[CH:25]=[C:26]([N+:29]([O-:31])=[O:30])[C:27]=1[OH:28])[CH3:18]

Participants

Conditions

Temperature: 79 °C

Procedure

A mixture of 1-(3-hydroxyphenyl)-2-phenylethanone (Intermediate 64) (154 mg, 0.726 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (153.3 mg, 0.726 mmol), urea (130.7 mg, 2.178 mmol), concentrated hydrochloric acid (0.5 mL) in ethanol (2 mL) was refluxed at 79° C. for 50 h. Removed solvent and purified by preparative HPLC to give Compound 129 (110 mg, yield 33.9%). HNMR (DMSO-d6 400 MHz): δ 10.29 (s, 1H), 9.41 (s, 1H), 8.62 (d, J=1.6 Hz, 1H), 7.50 (s, 1H), 7.43 (d, J=2.0 Hz, 1H), 7.19 (d, J=2.0 Hz, 1H), 7.05-6.97 (m, 4H), 6.83-6.80 (m, 2H), 6.65-6.58 (m, 3H), 5.12 (d, J=2.8 Hz, 1H), 4.05-4.02 (m, 2H), 1.34-1.30 (m, 3H); MS (ESI): m/z 448.0 [M+H]+.

Workup

customRemoved solvent and purified by preparative HPLC

Sources & evidence

ORD record: ord-b8131132cff1432db3850294e76a3a40
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09283229B2

Reaction notes

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