1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 52950706, compound

HRID 83039Notes

Reaction equation

HRID 83039 reaction equation
[F:1][C:2]([F:12])([F:11])[CH2:3][CH2:4][CH2:5][O:6][CH:7]1[CH2:10][NH:9][CH2:8]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.Cl.[O:44]=[C:45]1[NH:54][C:53]2[N:52]=[CH:51][C:50](/[CH:55]=[CH:56]/[C:57](O)=[O:58])=[CH:49][C:48]=2[CH2:47][CH2:46]1>CN(C)C=O.C(OCC)(=O)C.O>[O:58]=[C:57]([N:9]1[CH2:8][CH:7]([O:6][CH2:5][CH2:4][CH2:3][C:2]([F:1])([F:11])[F:12])[CH2:10]1)/[CH:56]=[CH:55]/[C:50]1[CH:49]=[C:48]2[C:53](=[N:52][CH:51]=1)[NH:54][C:45](=[O:44])[CH2:46][CH2:47]2

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 67154486HCID 67154486, compound

Product 1

HCID 52950706HCID 52950706, compoundYield 351.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(4,4,4-Trifluorobutoxy)-azetidine (129 mg, 0.59 mmol), EDCI (113 mg, 0.59 mmol), HOBt (80 mg, 0.59 mmol) and diisopropylethylamine (170 μL, 0.97 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 (100 mg, 0.039 mmol) in dimethylformamide (10 mL) at room temperature. The reaction mixture was stirred overnight then diluted with ethyl acetate (50 mL) and water (50 mL). The aqueous layer was separated and extracted with ethyl acetate (2×50 mL). The combined organic phases were washed with a saturated solution of sodium chloride (3×100 mL), dried over sodium sulfate and concentrated to dryness. The residue was purified by chromatography on silica gel using dichloromethane/methanol (95:5 to 9:1) as eluent. The residue was finally triturated in diethylether to give the title product as a pale yellow solid (52.5 mg, 35%).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washThe combined organic phases were washed with a saturated solution of sodium chloride (3×100 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by chromatography on silica gel
  7. customThe residue was finally triturated in diethylether

Sources & evidence

ORD record
ord-138d9bc4bbd64e6dacb77feb2d83dbde
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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