Hydrochloric Acid → HCID 66826163, compound

HRID 924895Notes

Reaction equation

[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=O)[CH:6]=[CH:7][CH:8]=1)[CH3:2].[CH2:18]([O:20][C:21]1[CH:22]=[C:23]([CH:26]=[C:27]([N+:30]([O-:32])=[O:31])[C:28]=1[OH:29])[CH:24]=O)[CH3:19].[NH2:33][C:34]([NH2:36])=[O:35].Cl>C(O)C>[CH2:18]([O:20][C:21]1[CH:22]=[C:23]([CH:24]2[C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[CH:4]=3)=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:36][C:34](=[O:35])[NH:33]2)[CH:26]=[C:27]([N+:30]([O-:32])=[O:31])[C:28]=1[OH:29])[CH3:19]

Participants

Conditions

Temperature: 115 °C

Procedure

A mixture of 2-(3-ethylphenyl)-1-phenylethanone (Intermediate 74) (90 mg, 0.40 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (84.5 mg, 0.40 mmol), urea (72 mg, 1.2 mmol), conc. HCl (0.2 mL) in ethanol (1 mL) was stirred at 115° C. for 6 h. Solvent was removed in vacuo and purification by prep-HPLC (0.1% TFA as additive) gave Compound 141 (46.3 mg, yield 25%). 1H NMR (DMSO 400 MHz): δ 10.29 (brs, 1H), 8.71 (s, 1H), 7.54 (s, 1H), 7.46 (s, 1H), 7.28-7.20 (m, 5H), 6.97-6.91 (m, 1H), 7.43 (d, J=7.6 Hz, 1H), 6.71-6.61 (m, 2H), 5.22 (d, J=2.8 Hz, 1H), 4.04 (q, J=6.8 Hz, 2H), 2.29 (q, J=7.6 Hz, 2H) 1.33 (t, J=6.8 Hz, 3H), 0.85 (t, J=7.6 Hz, 3H), MS (ESI): m/z 460.3 [M+H]+.

Workup

customSolvent was removed in vacuo and purification by prep-HPLC (0.1% TFA as additive)

Sources & evidence

ORD record: ord-d980d7be0dec42308a679656e1ec4cd8
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09283229B2

Reaction notes

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