Hydrochloric Acid → HCID 56961511, compound

HRID 401112Notes

Reaction equation

[OH:1][C:2]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[C:17]1([C:23](=O)[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[NH2:32][C:33]([NH2:35])=[O:34].Cl>C(O)C>[OH:1][C:2]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][C:5]([CH:6]2[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:23]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[NH:35][C:33](=[O:34])[NH:32]2)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15]

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 4-hydroxy-3-nitro-5-(trifluoromethyl)benzaldehyde (Intermediate 79) (100 mg, 0.40 mmol), 1,2-diphenylethanone (83 mg, 0.40 mmol), urea (77 mg, 1.30 mmol) and conc. HCl (0.05 mL) in ethanol (1 mL) was heated at 90° C. for 37 hours. Solvent was removed under reduced pressure and the residue was purified by prep-HPLC (0.1% TFA as additive) to give Compound 154 (31.2 mg, yield 30%) as yellow solid. 1H NMR (DMSO 300 MHz): δ 8.81 (s, 1H), 8.17 (s, 1H), 7.87 (s, 1H), 7.62 (s, 1H), 7.25-7.17 (m, 5H), 7.03-6.96 (m, 3H), 6.78 (d, J=7.2 Hz, 2H), 5.34 (s, 1H), MS (ESI): m/z 456.0 [M+H]+.

Workup

customSolvent was removed under reduced pressure
customthe residue was purified by prep-HPLC (0.1% TFA as additive)

Sources & evidence

ORD record: ord-405a1969a837401fbd00af2100aa42d5
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741915B2

Reaction notes

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