1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 52950618, compound

HRID 633949Notes

Reaction equation

HRID 633949 reaction equation
Cl.[CH2:2]([O:6][CH:7]1[CH2:10][NH:9][CH2:8]1)[CH2:3][CH2:4][CH3:5].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.Cl.[O:42]=[C:43]1[NH:52][C:51]2[N:50]=[CH:49][C:48](/[CH:53]=[CH:54]/[C:55](O)=[O:56])=[CH:47][C:46]=2[CH2:45][CH2:44]1>CN(C)C=O.O.C(OCC)(=O)C>[CH2:2]([O:6][CH:7]1[CH2:10][N:9]([C:55](=[O:56])/[CH:54]=[CH:53]/[C:48]2[CH:47]=[C:46]3[C:51](=[N:50][CH:49]=2)[NH:52][C:43](=[O:42])[CH2:44][CH2:45]3)[CH2:8]1)[CH2:3][CH2:4][CH3:5]

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 67154642HCID 67154642, compound

Product 1

HCID 52950618HCID 52950618, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Butoxyazetidine hydrochloride (100 mg, 0.6 mmol), EDCI (113 mg, 0.6 mmol), HOBt (80 mg, 0.6 mmol) and diisopropylethylamine (170 μL, 1.0 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, 0.4 mmol) in dimethylformamide (10 mL) at room temperature. The reaction mixture was stirred overnight and then partioned between ethyl acetate (30 mL) and water (30 mL). The aqueous layer was separated and extracted successively with ethyl acetate (2×20 mL) and dichloromethane (2×20 mL). The combined organic phases were washed with a saturated solution of sodium chloride (3×20 mL), dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel, using dichloromethane/methanol (99:1 to 97:3) as eluent. The title product was obtained as a grey solid (30 mg, 23%).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted successively with ethyl acetate (2×20 mL) and dichloromethane (2×20 mL)
  3. washThe combined organic phases were washed with a saturated solution of sodium chloride (3×20 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-227a89a9c9d94e2782e23cff410762e4
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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