4-Chloro-N-methylbenzenamine → HCID 9925034, compound

HRID 1435739Notes

Reaction equation

ClC1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[CH3:15])[N:5]=[C:4]([NH2:16])[N:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][CH3:25])=[CH:20][CH:19]=1.[CH:26](N(C(C)C)CC)(C)C>O1CCCC1>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]([CH3:15])=[C:8]([C:6]2[N:7]=[C:25]([N:24]([C:21]3[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=3)[CH3:26])[N:3]=[C:4]([NH2:16])[N:5]=2)[CH:13]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 4-chloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazin-2-yl-amine (106 mg, 0.42 mmol), (4-chloro-phenyl)-methyl-amine (0.15 ml, 1.25 mmol), tetrahydrofuran (5 ml), and diisopropylethylamine (0.75 ml, 4.2 mmol) was heated at 40° C. for 72 hours. The mixture was concentrated under reduced pressure and the residue was dissolved in dichloromethane (25 ml). The solution was washed with hydrochloric acid (1 M, 25 ml) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 2% methanol-dichloromethane followed by 5% methanol-dichloromethane. Recrystallization (ethyl acetate-hexane) provided the title compound (33 mg, 22% yield). 1H NMR (DMSO-d6) 7.78 (s, 1H), 7.37-7.46 (m, 4H), 7.26 (d, J=8.4 Hz, 1H), 7.10 (br s, 2H), 3.43 (s, 3H), 2.37 (s, 3H).

Workup

concentrationThe mixture was concentrated under reduced pressure
dissolutionthe residue was dissolved in dichloromethane (25 ml)
washThe solution was washed with hydrochloric acid (1 M, 25 ml)
concentrationconcentrated under reduced pressure
customThe residue was purified by flash chromatography on silica gel eluting with 2% methanol-dichloromethane
customRecrystallization (ethyl acetate-hexane)

Sources & evidence

ORD record: ord-682b5e661728461c8974931673772162
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618968B2

Reaction notes

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