Triethylamine → 3-Cyano-5-(3-hydroxy-benzylcarbamoyl)-thiophene-2-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:12]([OH:14])=O)=[CH:8][C:9]=1[C:10]#[N:11])=[O:4].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[NH2:56][CH2:57][C:58]1[CH:59]=[C:60]([OH:64])[CH:61]=[CH:62][CH:63]=1>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:12](=[O:14])[NH:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[C:60]([OH:64])[CH:59]=2)=[CH:8][C:9]=1[C:10]#[N:11])=[O:4]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-Cyano-thiophene-2,5-dicarboxylic acid 2-methyl ester (130 mg, 0.62 mmol) in anhydrous DMF (8 mL) was added triethylamine (0.26 mL, 1.86 mmol), HBTU (0.28 g, 0.74 mmol), HOBT (100 mg, 0.74 mmol), and 3-Aminomethyl-phenol (114 mg, 0.92 mmol). The mixture was stirred at room temperature 15 h, then quenched by pouring into EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography with 0-50% EtOAc in hexane to afford the desired product (0.033 g, 17% yield).
Workup
- customquenched
- additionby pouring into EtOAc
- washThe organic layer was washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- customThe residue was purified by flash chromatography with 0-50% EtOAc in hexane
Sources & evidence
- ORD record
- ord-c479740b95d74cb1b3a25642733341ef
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08404859B2
Reaction notes
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