Formic Acid → [5-amino-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]formamide
Reaction equation
S([O:5][CH2:6][CH2:7][N:8]1[C:12]([NH2:13])=[C:11]([NH2:14])[CH:10]=[N:9]1)(O)(=O)=O.C(N(CC)CC)C.[C:22](OC(=O)C)(=[O:24])C.C(O)=O>ClCCl.[Cl-].[Na+].O>[NH2:13][C:12]1[N:8]([CH2:7][CH2:6][OH:5])[N:9]=[CH:10][C:11]=1[NH:14][CH:22]=[O:24]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of 2-(4,5-diamino-1H-pyrazol-1-yl)ethanol sulfate (5 g) in dichloromethane (50 ml) was added triethylamine (6.38 ml) at 0° C., and the mixture was stirred at 0° C. for 10 minutes. A mixture of acetic anhydride (2.16 ml) and formic acid (1.74 ml) was stirred at 40° C. for 30 minutes, cooled to 0° C. and added dropwise to the above solution at 0° C. The whole mixture was stirred at 0° C. for 2 hours. To the mixture was added brine, and the whole mixture was extracted with tetrahydrofuran. The extract was dried over magnesium sulfate and evaporated under reduced pressure to give crude [5-amino-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]formamide, which was used in the next reaction without further purification.
Workup
- stirringwas stirred at 40° C. for 30 minutes
- temperaturecooled to 0° C.
- additionadded dropwise to the above solution at 0° C
- stirringThe whole mixture was stirred at 0° C. for 2 hours
- extractionthe whole mixture was extracted with tetrahydrofuran
- dry with materialThe extract was dried over magnesium sulfate
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-4ec120488a2948afb6a0e318d06e4578
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07129232B2
Reaction notes
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