Hydrochloric Acid → HCID 10368851, compound

HRID 2108682Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:16])[C:5]([N+:23]([O-:25])=[O:24])=[CH:4][N:3]=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:36])[CH3:35])=[CH:29][CH:28]=1.Cl.C(OCC)C>CC(O)C>[ClH:1].[C:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH:8][C:6]1[C:5]([N+:23]([O-:25])=[O:24])=[CH:4][N:3]=[C:2]([NH:26][C:27]2[CH:28]=[CH:29][C:30]([NH:33][C:34](=[O:36])[CH3:35])=[CH:31][CH:32]=2)[N:7]=1)(=[O:16])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of {2-[(2-chloro-5-nitropyrimidin-4-yl)amino]phenyl}(phenyl)-methanone (63 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 approx. 18 hours. After the reaction was cooled to room temperature cold diethyl ether was added to precipitate out the product. The precipitate was filtered and washed with cold diethyl ether, then dried under vacuum to give N-[4-({4-[(2-benzoylphenyl)amino]-5-nitropyrimidin-2-yl}amino)phenyl]acetamide hydrochloride (12 mg, 13%) as a tan solid. 1H NMR (DMSO-d6/D2O): δ 8.98 (s, 1H), 8.12 (m, 1H), 7.69-7.43 (m, 12 H), 2.05 (s, 3 H). MS m/z 468 (M+1).

Workup

additionwas added
customto precipitate out the product
filtrationThe precipitate was filtered
washwashed with cold diethyl ether
customdried under vacuum

Sources & evidence

ORD record: ord-71517eb6416a48b8a9b3c13f92a9f24c
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514446B2

Reaction notes

Loading…