1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 67118658, compound

HRID 1189011Notes

Reaction equation

HRID 1189011 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:21][C:22]2[CH:23]=[N:24][C:25]([CH2:28][O:29][CH3:30])=[CH:26][CH:27]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][C:18](O)=[O:19])[CH2:15][N:16]=1)=[CH:8]2.Cl.[CH2:32]([N:34]=C=NCCCN(C)C)[CH3:33].O.ON1C2C=CC=CC=2N=N1.O1CCCC1.C(N)C>CN(C)C=O>[CH2:32]([NH:34][C:18](=[O:19])[CH2:17][CH:14]1[S:13][C:12]([C:9]2[NH:10][C:11]3[C:7]([CH:8]=2)=[CH:6][C:5]([O:21][C:22]2[CH:23]=[N:24][C:25]([CH2:28][O:29][CH3:30])=[CH:26][CH:27]=2)=[CH:4][C:3]=3[O:2][CH3:1])=[N:16][CH2:15]1)[CH3:33]

Participants

6

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66726184Ethylamine tetrahydrofuranHCID 67118679HCID 67118679, compound

Product 1

HCID 67118658HCID 67118658, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of [2-(7-methoxy-5-{[6-(methoxymethyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetic acid (300 mg), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (268 mg), 1-hydroxybenzotriazole monohydrate (214 mg), 2M ethylamine tetrahydrofuran solution (0.7 mL) and N,N-dimethylformamide (10 mL) was stirred at room temperature for 16 h. The mixture was concentrated under reduced pressure. The residue was dissolved in water and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by basic silica gel column chromatography (methanol/ethyl acetate/hexane=0/70/30 to 8/92/0, volume ratio) to give a pale yellow amorphous solid. The amorphous solid was crystallized from acetonitrile to give white crystals. The crystals were recrystallized from acetonitrile to give the title compound (222 mg, 70%) as colorless crystals. MS 455 (MH+). mp 130-132° C.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by basic silica gel column chromatography (methanol/ethyl acetate/hexane=0/70/30 to 8/92/0, volume ratio)
  9. customto give a pale yellow amorphous solid
  10. customThe amorphous solid was crystallized from acetonitrile
  11. customto give white crystals
  12. customThe crystals were recrystallized from acetonitrile

Sources & evidence

ORD record
ord-86fd10e51379404aa55eaa86929dea44
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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