Hydrochloric Acid → HCID 51348809, compound

HRID 401063Notes

Reaction equation

[CH3:1][N:2]([CH3:18])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=O)=[CH:5][CH:4]=1.[CH2:19]([O:21][C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([N+:31]([O-:33])=[O:32])[C:29]=1[OH:30])[CH:25]=O)[CH3:20].[NH2:34][C:35]([NH2:37])=[O:36].Cl>C(O)C>[CH3:1][N:2]([CH3:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:25]([C:24]3[CH:27]=[C:28]([N+:31]([O-:33])=[O:32])[C:29]([OH:30])=[C:22]([O:21][CH2:19][CH3:20])[CH:23]=3)[NH:34][C:35](=[O:36])[NH:37][C:10]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 2-(4-(dimethylamino)phenyl)-1-phenylethanone (Intermediate 44) (235 mg, 1 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (212 mg, 1 mmol), and urea (138 mg, 3 mmol) in 10 mL of ethanol was added 0.2 mL of concentrated HCl solution, and the mixture was stirred at 130° C. for 2 days. After the solvent was removed under reduced pressure, the residue was purified by preparative HPLC (40-80% acetonitrile+0.1% trifluoroacetic acid in water, over 15 min.) to give the Compound 88 (65 mg, yield 13.9%). 1H NMR (CD3OD 400 MHz): δ 7.43 (s, 1H), 7.25-7.19 (m, 8H), 7.02 (d, J=8.4 Hz, 2H), 5.30 (s, 1H), 4.06-4.00 (m, 2H), 3.06 (s, 6H), 1.33 (t, J=6.8 Hz, 3H); MS (ESI): m/z 475.3 [M+1]+.

Workup

customAfter the solvent was removed under reduced pressure
customthe residue was purified by preparative HPLC (40-80% acetonitrile+0.1% trifluoroacetic acid in water, over 15 min.)

Sources & evidence

ORD record: ord-1bbd4509869548b88fdd8bc1ae2c8c89
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741915B2

Reaction notes

Loading…