Triethylamine → HCID 69242804, compound

HRID 2242186Notes

Reaction equation

HRID 2242186 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([O-:7])=O)[CH:3]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[C:44]([O:48][C:49]([N:51]1[CH2:55][C@@H:54]([CH2:56][NH2:57])[CH2:53][C@H:52]1[C:58]([N:60]1[CH2:64][CH2:63][S:62][CH2:61]1)=[O:59])=[O:50])([CH3:47])([CH3:46])[CH3:45]>CN(C)C=O>[C:44]([O:48][C:49]([N:51]1[CH2:55][C@@H:54]([CH2:56][NH:57][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([C:1]([O:12][CH3:13])=[O:11])[CH:3]=2)[CH2:53][C@H:52]1[C:58]([N:60]1[CH2:64][CH2:63][S:62][CH2:61]1)=[O:59])=[O:50])([CH3:47])([CH3:45])[CH3:46]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69512791,3-Benzenedicarboxylic acid, monomethyl esterHCID 69241294HCID 69241294, compound

Product 1

HCID 69242804HCID 69242804, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of monomethyl isophthalate (226 mg, 1.26 mmol) in anhydrous N,N-dimethylformamide (8 mL) was added 1-hydroxybenzotriazole monohydrate (204 mg, 1.51 mmol), followed by 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (288 mg, 1.51 mmol) and triethylamine (0.180 mL, 1.26 mmol). The mixture was stirred at room temperature for 30 minutes followed by the addition of a solution of Example 17D (380 mg, 1.2 mmol) in anhydrous N,N-dimethylformamide (2 mL). The mixture was allowed to stir at room temperature for 16 hours, concentrated under reduced pressure. The residue was diluted with dichloromethane (20 mL) and extracted with 1 M HCl (20 mL), saturated sodium bicarbonate (20 mL) and brine (20 mL) respectively. The organic layer was separated and dried (Na2SO4), filtered and concentrated to a light yellow oily solid which was chromatographed on a Biotage 40M with ethyl acetate to provide the titled compound. MS (APCI) m/e 478 (M+H)+.

Workup

  1. stirringto stir at room temperature for 16 hours
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with dichloromethane (20 mL)
  4. extractionextracted with 1 M HCl (20 mL), saturated sodium bicarbonate (20 mL) and brine (20 mL) respectively
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated to a light yellow oily solid which
  9. customwas chromatographed on a Biotage 40M with ethyl acetate

Sources & evidence

ORD record
ord-6bfc1291065247aea3a2094dbfa19393
Source dataset
uspto-grants-2010_03
Patent number
US07671076B2

Reaction notes

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