Ammonia → HCID 10290898, compound

HRID 1591625Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[CH3:16])[N:3]=1.[CH:17]([C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1)=[CH2:18].C([N:29](CC)C(C)C)(C)C.N>O1CCCC1>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]([CH3:16])=[C:9]([C:4]2[N:5]=[C:6]([NH:25][C:22]3[CH:23]=[CH:24][C:19]([CH:17]=[CH2:18])=[CH:20][CH:21]=3)[N:7]=[C:2]([NH2:29])[N:3]=2)[CH:14]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A mixture of 2,4-dichloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazine (500 mg, 1.8 mmol), 4-vinylphenylamine (228 mg, 1.9 mmol), tetrahydrofuran (20 ml), and N,N-diisopropylethylamine (0.63 ml, 3.6 mmol) was stirred for 2 hours. The mixture was transferred to a pressure bottle and chilled to −78° C. A slow stream of ammonia gas was passed into the mixture for 2 minutes and the bottle was sealed. After stirring at room temperature for 60 hours, the mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3) to provide the title compound (260 mg, 41% yield). 1H NMR (acetone-d6) 8.78 (br s, 1H), 7.92 (d, J=2.4 Hz, 1H), 7.88 (d, J=8.3 Hz, 2H), 7.44 (d, J=8.6 Hz, 2H), 7.39 (dd, J=2.4 Hz, J=8.2 Hz, 1H), 7.30 (d, J=8.2 Hz, 1H), 6.74 (dd, J=11.0 Hz, J=17.6 Hz, 1H), 6.64 (br s, 1H), 5.73 (dd, J=1.0 Hz, J=17.6 Hz, 1H), 5.15 (dd, J=1.0 Hz, J=11.0 Hz, 1H), 2.61 (s, 3H).

Workup

customthe bottle was sealed
stirringAfter stirring at room temperature for 60 hours
concentrationthe mixture was concentrated under reduced pressure
customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3)

Sources & evidence

ORD record: ord-bfc14fa99c464d99ae3b3aea3e24da60
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291616B2

Reaction notes

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