Diisopropylethylamine → HCID 86753076, compound

HRID 2393107Notes

Reaction equation

HRID 2393107 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH:13]([C:17]([CH3:21])([CH3:20])[CH2:18][CH3:19])[C:14](O)=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.CCN=C=NCCCN(C)C.Cl.OC1C2N=NNC=2C=CC=1.C(N(C(C)C)CC)(C)C.Cl.[NH2:54][OH:55]>CN(C=O)C.ClCCl>[OH:55][NH:54][C:14](=[O:15])[CH:13]([NH:12][S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10])[C:17]([CH3:21])([CH3:20])[CH2:18][CH3:19]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochloride2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 54447215HCID 54447215, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 86753076HCID 86753076, compoundYield 18.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The product of step 1 (0.116 g), EDC hydrochloride (0.076 g, 1.1 equivalent), hydroxybenzotriazole (0.054 g, 1.1 equivalent), and diisopropylethylamine (0.143 g, 3 equivalent) are mixed with dichloromethane (20 mL) to give a homogeneous solution. Hydroxylamine hydrochloride (0.051 g, 2 equivalent) is added as a solid. DMF (3 mL) is added to solubilize the hydroxylamine hydrochloride. The reaction is allowed to stir at room temperature overnight. The solvents are then removed under reduced pressure and the residue partitioned between ethyl acetate and 1N HCl. The organic phase is separated and the aqueous phase re-extracted with ethyl acetate. The combined organic phases are dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product is loaded onto a reverse phase column as a DMSO solution. The column is eluted with a step gradient, starting at 20% acetonitrile/water, and raised in 10% increments. The appropriate fractions are combined to give 22 mg of the title compound. 1H NMR (DMSO, 300 MHz): 10.4, 7.69-7.65, 7.43, 7.01-6.98, 3.80, 1.20-1.17, 0.77, 0.75, 0.69 .

Workup

  1. customto give a homogeneous solution
  2. customThe solvents are then removed under reduced pressure
  3. customthe residue partitioned between ethyl acetate and 1N HCl
  4. customThe organic phase is separated
  5. extractionthe aqueous phase re-extracted with ethyl acetate
  6. dry with materialThe combined organic phases are dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. washThe column is eluted with a step gradient
  10. temperatureraised in 10% increments

Sources & evidence

ORD record
ord-76c598b10f6f4f4b802d016fbc0416b9
Source dataset
uspto-grants-1998_09
Patent number
US05804593

Reaction notes

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