Pyridine → N-{1-Ethyl-3-[2-oxo-2(1-pyrrolidinyl)ethyl]-1H-pyrazol-5-yl}-2,2,2-trifluoroacetamide
Reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([O:5]C1C(F)=C(F)C(F)=C(F)C=1F)=O.[NH2:19][C:20]1[N:24]([CH2:25][CH3:26])[N:23]=[C:22]([CH2:27][C:28]([OH:30])=O)[CH:21]=1.[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33]C=1.N1CCCC1>CN(C=O)C>[CH2:25]([N:24]1[C:20]([NH:19][C:3](=[O:5])[C:2]([F:1])([F:17])[F:18])=[CH:21][C:22]([CH2:27][C:28](=[O:30])[N:31]2[CH2:33][CH2:34][CH2:35][CH2:36]2)=[N:23]1)[CH3:26]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Pentafluorophenyl trifluoroacetate (497 mg, 1.773 mmol) was added dropwise to a stirred solution of (5-amino-1-ethyl-1H-pyrazol-3-yl) acetic acid (150 mg, 0.887 mmol) and pyridine (0.143 mL, 1.773 mmol) in DMF (3 mL). The reaction mixture was stirred for 15 min and pyrrolidine (0.220 mL, 2.66 mmol) was added. The reaction mixture was stirred at 65° C. for 40 min. The mixture was cooled and quenched with water (5 mL) and extracted with EtOAc (3×). The extract was dried over Na2SO4, filtered and concentrated. The residue was purified using RP-HPLC to give product (125 mg). MS: (M+H)+=318.8. 1H NMR (400 MHz, CHLOROFORM-d) ppm 1.32 (t, J=7.2 Hz, 3H), 1.87-2.06 (m, 4H), 3.46 (t, J=6.8 Hz, 2H), 3.53 (t, J=6.8 Hz, 2H), 3.66 (s, 2H), 4.07 (q, J=7.2 Hz, 2H), 5.30 (s, 1H).
Workup
- stirringThe reaction mixture was stirred at 65° C. for 40 min
- temperatureThe mixture was cooled
- customquenched with water (5 mL)
- extractionextracted with EtOAc (3×)
- dry with materialThe extract was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified
Sources & evidence
- ORD record
- ord-50ec0a766cd94d22991785bd4b462b84
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09446034B2
Reaction notes
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