1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 52950745, compound

HRID 83043Notes

Reaction equation

HRID 83043 reaction equation
Cl.[CH3:2]/[C:3](=[CH:10]\[CH3:11])/[CH2:4][O:5][CH:6]1[CH2:9][NH:8][CH2:7]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.Cl.[O:43]=[C:44]1[NH:53][C:52]2[N:51]=[CH:50][C:49](/[CH:54]=[CH:55]/[C:56](O)=[O:57])=[CH:48][C:47]=2[CH2:46][CH2:45]1>CN(C)C=O.O.C(OCC)(=O)C>[CH3:2]/[C:3](=[CH:10]\[CH3:11])/[CH2:4][O:5][CH:6]1[CH2:9][N:8]([C:56](=[O:57])/[CH:55]=[CH:54]/[C:49]2[CH:48]=[C:47]3[C:52](=[N:51][CH:50]=2)[NH:53][C:44](=[O:43])[CH2:45][CH2:46]3)[CH2:7]1

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66905305(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid HydrochlorideHCID 86672985(E)-3-(2-Methylbut-2-enyloxy)azetidine hydrochloride

Product 1

HCID 52950745HCID 52950745, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(E)-3-(2-Methylbut-2-enyloxy)azetidine hydrochloride (168 mg, 0.94 mmol), EDCI (182 mg, 0.94 mmol), HOBt (132 mg, 0.94 mmol) and diisopropylethylamine (276 μL, 1.58 mmol) were successively added to a solution of (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)-acrylic acid hydrochloride (161 mg, 0.63 mmol) in dimethylformamide (12 mL) at room temperature. The reaction mixture was stirred overnight then diluted by addition of ethyl acetate (40 mL) and water (40 mL). The aqueous layer was separated and extracted with ethyl acetate (2×40 mL). The combined organic phases were washed with a saturated solution of sodium chloride (3×50 mL), dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel using dichloromethane/methanol (98:2) as eluent. After trituration in diethyl ether, petroleum ether and methanol, the title product was obtained as a white solid (46 mg, 21%).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (2×40 mL)
  3. washThe combined organic phases were washed with a saturated solution of sodium chloride (3×50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-8b7b9e4164f2444aa733a1871d24bbf0
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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