Acetic Acid → HCID 178525786, compound
Reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]([OH:16])=[O:15])[CH2:9]2)[CH:5]=[CH:4][C:3]=1[N+:17]([O-])=O.C([O-])=O.[NH4+].[CH:24]1([C:27]2[N:32]=[C:31]([CH:33]=O)[CH:30]=[CH:29][N:28]=2)[CH2:26][CH2:25]1.C(O)(=O)C>CN(C)C=O.O.[Zn]>[CH:24]1([C:27]2[N:32]=[C:31]([C:33]3[NH:1][C:2]4=[N:7][C:6]([N:8]5[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]([OH:16])=[O:15])[CH2:9]5)=[CH:5][CH:4]=[C:3]4[N:17]=3)[CH:30]=[CH:29][N:28]=2)[CH2:26][CH2:25]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 45 °C
Procedure
(R)-1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylic acid, prepared during the previous step, was dissolved in a mixture of N,N-dimethylformamide (45.5 mL) and water (4.9 mL). Ammonium formate (1.925 g, 30.625 mmol) was added followed by zinc dust (1.05 g, 15.3 mmol). The reaction mixture was stirred at 45° C. for 16 h. The mixture was filtered and the filtrate was concentrated under reduced pressure. To the residue was added N,N-dimethylformamide (24.5 mL) followed by a solution of 2-cyclopropylpyrimidine-4-carbaldehyde in N,N-dimethylformamide (24.5 mL, 6.125 mmol, 0.25M) and acetic acid (3.675 mL, 61.25 mmol). The reaction mixture was stirred at 60° C. for 16 h. The solvent was removed under reduced pressure and the residue was purified via preparative HPLC to afford the title compound (0.637 g, 28.6%).
Workup
- filtrationThe mixture was filtered
- concentrationthe filtrate was concentrated under reduced pressure
- additionTo the residue was added N,N-dimethylformamide (24.5 mL)
- stirringThe reaction mixture was stirred at 60° C. for 16 h
- customThe solvent was removed under reduced pressure
- customthe residue was purified via preparative HPLC
Sources & evidence
- ORD record
- ord-b7c99b1bc3814fff9d0e21b844c2c7cd
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296745B2
Reaction notes
Loading…