Imidazole → HCID 178518499, compound

HRID 2037003Notes

Reaction equation

HRID 2037003 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-a62e9866ab5446fc8a0ac4ca2a2705f1
Source dataset
uspto-grants-2013_11
Patent number
US08575177B2

Reaction notes

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