Hydrochloric Acid → 3-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-(4-nitrophenyl)benzamide hydrochloride

HRID 547541Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

3-Amino-N-(4-nitrophenyl)benzamide (B1) (1.0 g, 3.89 mmol) and 4-chloro-6-methyl-2-pyrimidinylamine (A8) (569 mg, 3.89 mmol) were dissolved in warm 2-ethoxyethanol. (20 mL). Two drops c.HCl was then added to the reaction mixture and refluxed for 1 h. by this time TLC and mass spec. showed completion of the reaction. The reaction mixture was diluted with ethyl acetate and cooled to 20° C. The resulting precipitate was filtered, washed with more EtOAc and recrystallized from MeOH/EtOAc/Charcoal/Celite to give B2 (1.531 g, 98%); m.p (MeOH/EtOAc)>300° C.; 1H NMR [(CD3)2SO] δ12.86 (br s, 1 H, N+H), 10.90 (s, 1 H, NH), 10.80 (br s, 1 H, NH), 8.30-8.26 (m, 2H, ArH), 8.11-8.08 (m, 4 H, ArH), 7.80-7.78 (br m, 3 H, ArH & NH2), 7.56 (t, J=7.8 Hz, 1 H, ArH), 2.30 (s, 3 H, CH3); mass APCI+ 365.

Workup

temperaturerefluxed for 1 h. by this time TLC and mass spec
customcompletion of the reaction
filtrationThe resulting precipitate was filtered
washwashed with more EtOAc
customrecrystallized from MeOH/EtOAc/Charcoal/Celite

Sources & evidence

ORD record: ord-a810ab636f90487e8cc1276ce80ce470
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07939546B2

Reaction notes

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