Water → Methyl 4-[2-(3-dimethylaminobenzofuran-2-ylcarbonylamino)ethoxy]benzoate

HRID 713734Notes

Reaction equation

HRID 713734 reaction equation
CN(C[C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]=1[C:14]([OH:16])=O)C.CCN=C=NCCC[N:25]([CH3:27])[CH3:26].Cl.[CH:29]1[CH:30]=[CH:31][C:32]2N(O)N=N[C:33]=2[CH:34]=1.[OH2:39].[CH2:40]([N:42](CC)CC)[CH3:41].C[CH2:48][O:49][C:50](C)=[O:51]>CN(C=O)C>[CH3:27][N:25]([CH3:26])[C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]=1[C:14]([NH:42][CH2:40][CH2:41][O:39][C:29]1[CH:30]=[CH:31][C:32]([C:50]([O:49][CH3:48])=[O:51])=[CH:33][CH:34]=1)=[O:16]

Participants

8

Reactant 6

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 289433393-[(Dimethylamino)methyl]-1-benzofuran-2-carboxylic acid

Product 1

HCID 66688396Methyl 4-[2-(3-dimethylaminobenzofuran-2-ylcarbonylamino)ethoxy]benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-dimethylaminomethylbenzofuran-2-carboxylic acid (140 mg, 0.56 mmol) was added EDC.HCl (150 mg, 0.784 mmol) and HOBt.H2O (114 mg, 0.84 mmol) in anhydrous DMF. The reaction mixture was stirred for 30-60 min., after which methyl-(4-(2-ethoxyamine))benzoate hydrochloric salt (130 mg, 0.56 mmol) and triethylamine (94 μL, 0.672 mmol) were added and the reaction was stirred overnight. The reaction mixture was diluted with EtOAc and washed twice with saturated NaHCO3 (aq.) and brine. The organic extract was concentrated in vacuo to give methyl 4-[2-(3-dimethylaminobenzofuran-2-yl-carbonylamino)ethoxy]benzoate, which was then used without further purification.

Workup

  1. stirringthe reaction was stirred overnight
  2. washwashed twice with saturated NaHCO3 (aq.) and brine
  3. extractionThe organic extract
  4. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-9dc82d4978af4791be3c79cfb705dd8d
Source dataset
uspto-grants-2015_11
Patent number
US09186347B1

Reaction notes

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