2-(Methylamino)ethanol → HCID 59303890, compound

HRID 2238589Notes

Reaction equation

HRID 2238589 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([O:11][C:12]2[C:20]3[N:19]=[C:18]([CH3:21])[N:17]([CH3:22])[C:16]=3[CH:15]=[C:14]([C:23]([OH:25])=O)[CH:13]=2)[CH2:3][CH2:2]1.[CH3:26][NH:27][CH2:28][CH2:29][OH:30].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([O:11][C:12]2[C:20]3[N:19]=[C:18]([CH3:21])[N:17]([CH3:22])[C:16]=3[CH:15]=[C:14]([C:23]([N:27]([CH2:28][CH2:29][OH:30])[CH3:26])=[O:25])[CH:13]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 80162-(Methylamino)ethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 686891664-(3,4-Dihydro-2H-chromen-4-yloxy)-1,2-dimethyl-1H-benzimidazole-6-carboxylic acid

Product 1

HCID 59303890HCID 59303890, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 4-(3,4-dihydro-2H-chromen-4-yloxy)-1,2-dimethyl-1H-benzimidazole-6-carboxylic acid (70 mg, 0.21 mmol, STEP 2) and 2-(methylamino)ethanol (31 mg, 0.41 mmol) in dimethylformamide (2 mL) were added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCl) (67 mg, 0.35 mmol) and 1-hydroxybenzotriazole hydrate (HOBt) (60 mg, 0.41 mmol) at room temperature. After stirring at room temperature for 18 hours, the reaction mixture was quenched with sodium hydrogencarbonate aqueous solution (5 mL), and extracted with ethyl acetate (50 mL×2). The combined extracts were washed with brine, dried over sodium sulfate, and concentrated in vacuum. The residue was purified by column chromatography on silica gel (ethyl acetate:methanol=10:1 as an eluent). The residue was suspended with diethyl ether, and collected by filtration to afford the title compound as a white solid (24 mg, 24%):

Workup

  1. customthe reaction mixture was quenched with sodium hydrogencarbonate aqueous solution (5 mL)
  2. extractionextracted with ethyl acetate (50 mL×2)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuum
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-0751390cad4b4d93b1f7ca5c8cb102a3
Source dataset
uspto-grants-2010_05
Patent number
US07718809B2

Reaction notes

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