Hydrochloric Acid → HCID 51348364, compound

HRID 401040Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:14]2[C:19]([C:20]3[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=3)C#N)=C(C3C=CC=CC=3)[NH:17][C:16](=[O:34])[NH:15]2)[CH:7]=[C:8]([N+]([O-])=O)[C:9]=1[OH:10])C.[CH2:35]([O:37][C:38]1[CH:39]=[C:40]([CH:43]=[C:44]([N+:47]([O-:49])=[O:48])[C:45]=1[OH:46])[CH:41]=O)[CH3:36].NC(N)=O.Cl>C(O)C>[O:10]1[C:9]2[CH:8]=[CH:7][C:6]([C:14]3[NH:15][C:16](=[O:34])[NH:17][CH:41]([C:40]4[CH:43]=[C:44]([N+:47]([O-:49])=[O:48])[C:45]([OH:46])=[C:38]([O:37][CH2:35][CH3:36])[CH:39]=4)[C:19]=3[C:20]3[CH:27]=[CH:26][CH:25]=[CH:22][CH:21]=3)=[CH:5][C:4]=2[O:3][CH2:1]1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 1-(benzo[d][1,3]dioxol-5-yl)-2-phenylethanone (Intermediate 29) (400 mg, 1.7 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (352 mg, 1.7 mmol), and urea (230 mg, 5.0 mmol) in 10 mL of ethanol was added 0.2 mL of concentrated HCl solution, the mixture was stirred at 130° C. overnight. After the solvent was removed under reduced pressure, the residue was purified by preparative HPLC (35-65% acetonitrile+0.1% trifluoroacetic acid in water, over 15 min.) to give Compound 61 (92.5 mg, yield 11.7%). 1H NMR (CD3OD 400 MHz): δ 7.60 (s, 1H), 7.18 (s, 1H), 7.12-7.09 (m, 3H), 6.92 (d, J=7.2 Hz, 2H), 6.78 (d, J=8.0 Hz, 1H), 6.71 (m, 2H), 5.92 (s, 2H), 5.32 (s, 1H), 4.11-4.03 (m, 2H), 1.41 (t, J=7.2 Hz, 3H); MS (ESI): m/z 476.3 [M+1]+.

Workup

customAfter the solvent was removed under reduced pressure
customthe residue was purified by preparative HPLC (35-65% acetonitrile+0.1% trifluoroacetic acid in water, over 15 min.)

Sources & evidence

ORD record: ord-9ef33c7aeb904bfd922688ea3761d0d6
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741915B2

Reaction notes

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