Water → Methyl 4-{2-[3-(2,2,2-trifluoroethoxymethyl)benzofuran-2-yl-carbonylamino]ethoxy}benzoate

HRID 713737Notes

Reaction equation

HRID 713737 reaction equation
[F:1][C:2]([F:19])([F:18])[CH2:3][O:4][CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][C:7]=1[C:15]([OH:17])=O.CCN=C=NC[CH2:26][CH2:27][N:28](C)C.Cl.[CH:32]1[CH:33]=[CH:34][C:35]2N(O)N=N[C:36]=2[CH:37]=1.[OH2:42].C(N(CC)CC)C.C[CH2:51][O:52][C:53](C)=[O:54]>CN(C=O)C>[F:18][C:2]([F:1])([F:19])[CH2:3][O:4][CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][C:7]=1[C:15]([NH:28][CH2:27][CH2:26][O:42][C:32]1[CH:33]=[CH:34][C:35]([C:53]([O:52][CH3:51])=[O:54])=[CH:36][CH:37]=1)=[O:17]

Participants

8

Reactant 6

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 289432073-(2,2,2-Trifluoroethoxymethyl)benzofuran-2-carboxylic acid

Product 1

HCID 66688446Methyl 4-{2-[3-(2,2,2-trifluoroethoxymethyl)benzofuran-2-yl-carbonylamino]ethoxy}benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(2,2,2-trifluoroethoxymethyl)benzofuran-2-carboxylic acid (38 mg, 0.139 mmol) in anhydrous DMF was added EDC.HCl (37 mg, 0.195 mmol) and HOBt.H2O (26 mg, 0.195 mmol). After 60-90 min., methyl-(4-(2-ethoxyamine))benzoate hydrochloric salt (32 mg, 0.139 mmol) and triethylamine (23 μL, 0.167 mmol) were added and the reaction mixture was stirred for 1-2 h. The reaction mixture was diluted with EtOAc and washed twice with saturated NaHCO3(aq.) and the organic extract was concentrated to give methyl 4-{2-[3-(2,2,2-trifluoroethoxymethyl)benzofuran-2-yl-carbonylamino]ethoxy}benzoate, which was then used without further purification.

Workup

  1. washwashed twice with saturated NaHCO3(aq.)
  2. extractionthe organic extract
  3. concentrationwas concentrated

Sources & evidence

ORD record
ord-9c881febc6ac4d3d81abbda000f67d6f
Source dataset
uspto-grants-2015_11
Patent number
US09186347B1

Reaction notes

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