Hydrochloric Acid → HCID 10073764, compound

HRID 2108679Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=[O:12])[C:5]([N+:18]([O-:20])=[O:19])=[CH:4][N:3]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[NH2:26].Cl.C(OCC)C>CC(O)C>[ClH:1].[N+:18]([C:5]1[C:6]([NH:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=[O:12])=[N:7][C:2]([NH:26][C:25]2[CH:27]=[C:28]([O:32][CH3:33])[C:29]([O:30][CH3:31])=[C:23]([O:22][CH3:21])[CH:24]=2)=[N:3][CH:4]=1)([O-:20])=[O:19]

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 2-[(2-chloro-5-nitropyrimidin-4-yl)amino]benzoic acid (52 mg, 0.178 mmol) and 3,4,5-trimethoxyaniline (34 mg, 0.185 mmol) in 2-propanol (2 mL) was added 1N HCl in diethyl ether (50 uL, 0.05 mmol). The reaction mixture was heated at 90° C. for 30 hours. After the reaction was cooled to room temperature the mixture was filtered, and the solid was washed with 2-propanol, hexane, and ethyl acetate. The solid was then dried under vacuum to give 2-({5-nitro-2-[(3,4,5-trimethoxyphenyl)-amino]pyrimidin-4-yl}amino)benzoic acid hydrochloride (53 mg, 63%) as a dirty orange solid. 1H NMR (DMSO-d6/D2O): δ 9.14 (s, 1H), 8.47 (m, 1 H), 8.02 (d, 1 H), 7.46 (m, 1 H), 7.26 (t, 1 H), 6.95 (s, 2 H), 3.69 (s, 3 H), 3.63 (s, 6 H); MS m/z 441 (M+1).

Workup

temperatureAfter the reaction was cooled to room temperature the mixture
filtrationwas filtered
washthe solid was washed with 2-propanol, hexane, and ethyl acetate
customThe solid was then dried under vacuum

Sources & evidence

ORD record: ord-0e4fded3eca74e33abb9729644437b55
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514446B2

Reaction notes

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