Hydrochloric Acid → N-(2-Hydroxy-2-methylpropyl)-N,1-dimethyl-4-nitro-1H-pyrazole-3-carboxamide
Reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[C:4]([C:10]([OH:12])=O)=[N:3]1.[CH3:13][C:14]([OH:19])([CH3:18])[CH2:15][NH:16][CH3:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.Cl>C1COCC1>[OH:19][C:14]([CH3:18])([CH3:13])[CH2:15][N:16]([CH3:17])[C:10]([C:4]1[C:5]([N+:7]([O-:9])=[O:8])=[CH:6][N:2]([CH3:1])[N:3]=1)=[O:12]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a suspension of 1-methyl-4-nitro-1H-pyrazole-3-carboxylic acid (639 mg, 3.7 mmol) and 2-methyl-1-(methylamino)propan-2-ol (500 mg, 4.85 mmol) in THF (15 mL) were added HATU (1.57 g, 4.12 mmol) and N-methylmorpholine (2.13 mL, 19.4 mmol) at ambient temperature. The mixture was heated to 70° C. and stirred for 16 h. After cooling down to ambient temperature, the reaction mixture was poured into 20 mL HCl (2N aqueous solution) and extracted with ethyl acetate (2×100 mL). The organic layers were washed with water, brine and the solvent was evaporated. The aqueous layer was back-extracted with dichloromethane, dried and concentrated in vacuo. Both residues were combined to give 2.75 g of a semi-solid yellow material. The crude material was purified by silica gel chromatography using a methanol/ethyl acetate gradient to yield the product (1.2 g, 90%) as colorless oil.
Workup
- temperatureAfter cooling down to ambient temperature
- extractionextracted with ethyl acetate (2×100 mL)
- washThe organic layers were washed with water, brine
- customthe solvent was evaporated
- extractionThe aqueous layer was back-extracted with dichloromethane
- customdried
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-57ca65df24d64d289f04e6168662b11d
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08623866B2
Reaction notes
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