1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59436187, compound

HRID 2089804Notes

Reaction equation

HRID 2089804 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:18])[C:5]([C:15]([OH:17])=O)=[N:6][N:7]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[CH:8]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH3:41][NH:42][O:43][CH3:44]>CN(C=O)C>[CH3:44][O:43][N:42]([CH3:41])[C:15]([C:5]1[C:4](=[O:18])[C:3]([O:2][CH3:1])=[CH:8][N:7]([C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)[N:6]=1)=[O:17]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 59436260HCID 59436260, compound

Product 1

HCID 59436187HCID 59436187, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-methoxy-4-oxo-1-pyridin-4-yl-1,4-dihydropyridazine-3-carboxylic acid (8.2 g, 33 mmol), HOBt (7.6 g, 50 mmol) and WSC (9.5 g, 50 mmol) in DMF (160 mL) was added N,O-dimethylhydroxylamine hydrochloride (6.5 g, 66 mmol) and TEA (14 mL, 100 mmol), and the mixture was stirred at room temperature overweekend. The mixture was concentrated under reduced pressure. The residue was diluted with water, saturated with K2CO3, and extracted with AcOEt. (There were three layers.) The highest organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The middle layer was extracted with CH2Cl2 (50 mL×4), and the combined extracts were dried over MgSO4, filtered and concentrated under reduced pressure. Two of the residues were combined and chromatographed on basic silica gel (0/100-10/90 MeOH/AcOEt) to give the title compound (9.6 g, 100% yield) as a pale yellow oil: 1H NMR (300 MHz, CDCl3): δ ppm 3.40 (3H, s), 3.68 (3H, s), 3.98 (3H, s), 7.61 (2H, dd, J=4.8, 1.5 Hz), 8.08 (1H, s), 8.73 (2H, dd, J=4.8, 1.5 Hz).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with water, saturated with K2CO3
  3. extractionextracted with AcOEt
  4. dry with material(There were three layers.) The highest organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. extractionThe middle layer was extracted with CH2Cl2 (50 mL×4)
  8. dry with materialthe combined extracts were dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customchromatographed on basic silica gel (0/100-10/90 MeOH/AcOEt)

Sources & evidence

ORD record
ord-267fb4e791e44e2ea37f0ac66a770f03
Source dataset
uspto-grants-2013_05
Patent number
US08435995B2

Reaction notes

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