Imidazole → HCID 178518499, compound

HRID 624785Notes

Reaction equation

HRID 624785 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)[N:6]=2)[CH2:3][CH2:2]1.C1(NC2N3N=CC(/C=[C:39]4/[C:40](=O)[NH:41][C:42](=O)[NH:43]/4)=C3N=C(S(C)(=O)=O)N=2)CC1.N1C=CN=C1>C(O)(C)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]([N:41]3[CH:40]=[CH:39][N:43]=[CH:42]3)[N:6]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 178504622HCID 178504622, compoundHCID 178504850HCID 178504850, compound

Product 1

HCID 178518499HCID 178518499, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (Z)-5-((4-(cyclopropylamino)-2-(methylsulfinyl)pyrazolo[1,5-a][1,3,5]triazin-8-yl)methylene)imidazolidine-2,4-dione and (Z)-5-((4-(cyclopropylamino)-2-(methylsulfonyl)pyrazolo[1,5-a][1,3,5]triazin-8-yl)methylene)imidazolidine-2,4-dione (10 mg, 0.028 mmol) was mixed with imidazole (6 mg, 0.084 mmol) in isopropanol (1 mL). The mixture was stirred at 80° C. for 16 h. The reaction mixture was cooled to room temperature and the resulting solid was filtered off and washed with isopropanol. The solid was dried under vacuum to provide (Z)-5-((4-(cyclopropylamino)-2-(1H-imidazol-1-yl)pyrazolo[1,5-a][1,3,5]triazin-8-yl)methylene)imidazolidine-2,4-dione as a yellow solid. LCMS (ES): >95% pure, m/z 352 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe resulting solid was filtered off
  3. washwashed with isopropanol
  4. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-2327864711a541aca88dd384950ff949
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

Loading…