Isopropanol → HCID 178463446, compound

HRID 624784Notes

Reaction equation

[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13](/[CH:14]=[C:15]4/[C:16](=[O:21])[NH:17][C:18](=[O:20])[NH:19]/4)=[C:9]3[N:8]=[C:7](S(C)(=O)=O)[N:6]=2)[CH2:3][CH2:2]1.C1(NC2N3N=[CH:37][C:38](/[CH:39]=[C:40]4/[C:41](=O)[NH:42][C:43](=O)[NH:44]/4)=C3N=C(S(C)=O)N=2)CC1.[CH3:50]C(O)C>>[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13](/[CH:14]=[C:15]4/[C:16](=[O:21])[NH:17][C:18](=[O:20])[NH:19]/4)=[C:9]3[N:8]=[C:7]([NH:42][CH:41]([C:40]3[CH:39]=[CH:38][CH:37]=[CH:43][N:44]=3)[CH3:50])[N:6]=2)[CH2:3][CH2:2]1

Participants

Reactant 3

HCID 3776Isopropanol

HCID 178504622HCID 178504622, compound

HCID 178504850HCID 178504850, compound

Product 1

HCID 178463446HCID 178463446, compound

Conditions

Temperature: 90 °C

Procedure

A (2:1) 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 (1.0 eq, 3.6 g, 10.08 mmol) was suspended in 2-propanol (40 ml). Rac-1-pyridinil-2-yl-ethylamine (2.0 eq, 2.47 g, 20.22 mmol) was added and the mixture stirred at 90° C. for 6.5 hours. The mixture was cooled down and the solid isolated by filtration. After drying in a vacuum oven, (Z)-5-((4-(cyclopropylamino)-2-(1-(pyridin-2-yl)ethylamino)pyrazolo[1,5-a][1,3,5]triazin-8-yl)methylene)imidazolidine-2,4-dione was isolated as a pale yellow solid (3.60 g, 88%). LCMS (ES): >95% pure, m/z 406 [M+H]+.

Workup

temperatureThe mixture was cooled down
customthe solid isolated by filtration
customAfter drying in a vacuum oven

Sources & evidence

ORD record: ord-fcb2dfd874e3490f9750cdd48c799fff
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303033B2

Reaction notes

Loading…