Triethylamine → 5-[2-(3-Hydroxy-phenyl)-ethyl-carbamoyl]-3-methyl-thiophene-2-carboxylic acid methyl ester

HRID 1952569Notes

Reaction equation

HRID 1952569 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]([OH:13])=O)=[CH:8][C:9]=1[CH3:10])=[O:4].Cl.[OH:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[CH2:19][CH2:20][NH2:21].C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11](=[O:13])[NH:21][CH2:20][CH2:19][C:18]2[CH:22]=[CH:23][CH:24]=[C:16]([OH:15])[CH:17]=2)=[CH:8][C:9]=1[CH3:10])=[O:4]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 770013-(2-Aminoethyl)phenol hydrochlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 682266195-(Methoxycarbonyl)-4-methylthiophene-2-carboxylic acid

Product 1

HCID 682267035-[2-(3-Hydroxy-phenyl)-ethyl-carbamoyl]-3-methyl-thiophene-2-carboxylic acid methyl esterYield 162.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-methyl-thiophene-2,5-dicarboxylic acid 2-methyl ester (0.1 g, 0.5 mmol) and 3-hydroxyphenethylamine hydrochloride (105 mg, 0.6 mmol) in DMF (5 ml) was added at rt triethylamine (0.21 ml, 1.5 mmol), HOBT (81 mg, 0.6 mmol) and HBTU (230 mg, 0.6 mmol). The mixture was stirred at rt for 1 h, then quenched with 1NHCl and extracted with EtOAc. The layers were separated. The organic layer was washed with brine, then dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography with 15-65% EtOAc in hexane to afford the desired product (260 mg, 81% yield).

Workup

  1. customquenched with 1NHCl and
  2. extractionextracted with EtOAc
  3. customThe layers were separated
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography with 15-65% EtOAc in hexane

Sources & evidence

ORD record
ord-e8c500d4454340d7bce6129625354ae3
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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