Hydrochloric Acid → HCID 10072833, compound

HRID 2108685Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 2-[(2-chloro-5-nitropyrimidin-4-yl)amino]-N-methylbenzamide (54 mg, 0.178 mmol) and N-(4-aminophenyl)acetamide (28 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-[(2-{[4-(acetylamino)phenyl]amino}-5-nitropyrimidin-4-yl)amino]-N-methylbenzamide hydrochloride (58 mg, 71%) as a yellow tan solid. 1H NMR (DMSO-d6/D2O): δ 9.05 (s, 1H), 8.20 (m, 1H), 7.59 (d, 1 H), 7.40-7.50 (m, 5 H), 7.24 (t, 1 H), 2.76 (s, 3 H), 2.02 (s, 3H). MS m/z 421 (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-7e73e1b463944a78871ccb0d148be801
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514446B2

Reaction notes

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