Pyrrolidine → HCID 86679693, compound
Reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([OH:12])=O)=[N:8][CH:9]=1)([O-:3])=[O:2].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])=[N:8][CH:9]=1)([O-:3])=[O:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 5-nitropicolinic acid (CIII) (500 mg, 2.97 mmol) in DMF (15 mL) was added pyrrolidine (244 μl, 2.47 mmol) and DIPEA (1.03 mL, 5.95 mmol). The reaction was cooled at 0° C. before adding HATU (1.13 g, 2.47 mmol). The reaction was warmed to room temperature and stirred for 2 hrs. The reaction was concentrated under vacuum and then dissolved in a mixture of water and 10% iPrOH/CHCl3. The organic layer was separated and the aqueous phase was washed again with 10% iPrOH/CHCl3. The combined organic phases were washed with brine, dried over MgSO4 and evaporated to yield (5-nitropyridin-2-yl)(pyrrolidin-1-yl)methanone (CIV) as a red solid (849 mg). ESIMS found for C10H11N3O3 m/z 222.1 (M+H).
Workup
- temperatureThe reaction was warmed to room temperature
- concentrationThe reaction was concentrated under vacuum
- dissolutiondissolved in a mixture of water and 10% iPrOH/CHCl3
- customThe organic layer was separated
- washthe aqueous phase was washed again with 10% iPrOH/CHCl3
- washThe combined organic phases were washed with brine
- dry with materialdried over MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-ad206a64ef9a4bd19aa3483d158e2cc5
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221793B2
Reaction notes
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