Benzyl Alcohol → HCID 178518507, compound

HRID 624789Notes

Reaction equation

HRID 624789 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[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.O>[CH2:1]([O:8][C:17]1[N:16]=[C:15]([NH:14][CH:11]2[CH2:13][CH2:12]2)[N:20]2[N:21]=[CH:22][C:23](/[CH:24]=[C:25]3/[C:26](=[O:31])[NH:27][C:28](=[O:30])[NH:29]/3)=[C:19]2[N:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 178504622HCID 178504622, compoundHCID 178504850HCID 178504850, compound

Product 1

HCID 178518507HCID 178518507, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Benzyl alcohol (14.2 μL, 0.138 mmol) was dissolved in NMP (0.2 ml). Sodium Hydride (60%, 5.5 mg, 0.138 mmol) was added and the reaction stirred at room temperature for one hour. 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 (10 mg, 0.027 mmol) was added and the mixture was stirred at room temperature for one hour. Water was added and the material was extracted with ethyl acetate. After concentration at the rotary evaporator, addition of methanol formed a precipitate that was filtered and dried. (Z)-5-((2-(benzyloxy)-4-(cyclopropylamino)pyrazolo[1,5-a][1,3,5]triazin-8-yl)methylene)imidazolidine-2,4-dione was isolated as a solid (5.6 mg). LCMS (ES): >95% pure, m/z 392 [M+H]+.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for one hour
  3. extractionthe material was extracted with ethyl acetate
  4. concentrationAfter concentration
  5. customat the rotary evaporator, addition of methanol
  6. customformed a precipitate that
  7. filtrationwas filtered
  8. customdried

Sources & evidence

ORD record
ord-fba0206c28c04720a38a7f1275e735f0
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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