2-Methoxyethylamine → HCID 118656102, compound

HRID 591489Notes

Reaction equation

HRID 591489 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:27][C:28]1[CH:51]=[C:50]([Cl:52])[CH:49]=[CH:48][C:29]=1[CH2:30][O:31][C:32]1[CH:47]=[CH:46][C:35]2[C:36]([O:42][CH2:43][O:44][CH3:45])=[C:37]([C:39](O)=[O:40])[S:38][C:34]=2[CH:33]=1>O.CN(C=O)C>[Cl:27][C:28]1[CH:51]=[C:50]([Cl:52])[CH:49]=[CH:48][C:29]=1[CH2:30][O:31][C:32]1[CH:47]=[CH:46][C:35]2[C:36]([O:42][CH2:43][O:44][CH3:45])=[C:37]([C:39]([NH:5][CH2:4][CH2:3][O:2][CH3:1])=[O:40])[S:38][C:34]=2[CH:33]=1

Participants

7

Reactant 4

HCID 80182-MethoxyethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 89768204HCID 89768204, compound

Product 1

HCID 118656102HCID 118656102, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-methoxyethylamine (0.082 mL), EDCI (181 mg), HOBt (128 mg), 6-((2,4-dichlorobenzyl)oxy)-3-(methoxymethoxy)-1-benzothiophene-2-carboxylic acid (260 mg) and DMF (5 mL) was stirred at room temperature for 18 h. Water was added to the mixture, and the mixture was extracted with EtOAc. The EtOAc extract was washed successively with 1N HCl, saturated aqueous NaHCO3 and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (205 mg). The obtained crystals were recrystallized from EtOAc-hexane.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. extractionThe EtOAc extract
  3. washwas washed successively with 1N HCl, saturated aqueous NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-3966bfa155fa4d089d09dc549dd8e5f4
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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