Benzenemethanamine, 3,4-dimethyl- → HCID 178425513, compound

HRID 624783Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][NH2:10])[CH:5]=[CH:6][C:7]=1[CH3:8].[CH:11]1([NH:14][C:15]2[N:20]3[N:21]=[CH:22][C:23](/[CH:24]=[C:25]4/[C:26](=[O:31])[NH:27][C:28](=[O:30])[NH:29]/4)=[C:19]3[N:18]=[C:17](S(C)(=O)=O)[N:16]=2)[CH2:13][CH2:12]1.C1(NC2N3N=CC(/C=C4/C(=O)NC(=O)N/4)=C3N=C(S(C)=O)N=2)CC1>CN1C(=O)CCC1>[CH:11]1([NH:14][C:15]2[N:20]3[N:21]=[CH:22][C:23](/[CH:24]=[C:25]4/[C:26](=[O:31])[NH:27][C:28](=[O:30])[NH:29]/4)=[C:19]3[N:18]=[C:17]([NH:10][CH2:9][C:4]3[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=3)[N:16]=2)[CH2:12][CH2:13]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of (3,4-dimethylphenyl)methanamine in NMP (106 μl, 0.4 M, 1.5 eq, 0.042 mmol) was transferred in a glass reaction vial. A solution of a (1:1) mixture of (Z)-5-((4-(cyclopropylamino)-2-(methylsulfonyl)pyrazolo[1,5-a][1,3,5]triazin-8-yl)methylene)imidazolidine-2,4-dione and (Z)-5-((4-(cyclopropylamino)-2-(methylsulfinyl)pyrazolo[1,5-a][1,3,5]triazin-8-yl)methylene)imidazolidine-2,4-dione in NMP (100 μl, 0.282M, 1.0 eq, 0.0282 mmol) was added. The mixture was heated at 80° C. for 5 hours. NMP was added (0.7 ml) and the solution subjected to preparative HPLC purification. Genevac evaporation provided (Z)-5-((4-(cyclopropylamino)-2-(3,4-dimethylbenzylamino)pyrazolo[1,5-a][1,3,5]triazin-8-yl)methylene)imidazolidine-2,4-dione as a solid (5.8 mg). LCMS (ES): >85% pure, m/z 419 [M+H]+.

Workup

additionwas added
customthe solution subjected to preparative HPLC purification
customGenevac evaporation

Sources & evidence

ORD record: ord-8539bd76c349454aa0cc2b47dcbc781a
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303033B2

Reaction notes

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