1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 52950792, compound

HRID 2172131Notes

Reaction equation

HRID 2172131 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.[CH:32]([N:35]([CH:38]([CH3:40])C)[CH2:36][CH3:37])(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])[C:44]2([CH2:37][CH2:36][N:35]([CH3:32])[CH2:38][CH2:40]2)[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 52950792HCID 52950792, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Butoxyazetidine hydrochloride (33 mg, 0.20 mmol), EDCI (72 mg, 0.4 mmol), HOBt (54 mg, 0.4 mmol) and diisopropylethylamine (116 μL, 0.66 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 (45 mg, 0.13 mmol) in dimethylformamide (5 mL) at room temperature. The reaction mixture was stirred overnight and then diluted by addition of ethyl acetate (40 mL) and water (40 mL). The aqueous phase was extracted with ethyl acetate (2×40 mL). The combined organic phases were washed with a saturated solution of sodium chloride (3×40 mL), dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel using dichloromethane/methanol (7:3 to 5:5) as eluent. After precipitation in DCM/Et2O and triturations in acetone, the title product was obtained as a white solid (10 mg, 17%).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate (2×40 mL)
  2. washThe combined organic phases were washed with a saturated solution of sodium chloride (3×40 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by chromatography on silica gel
  7. customAfter precipitation in DCM/Et2O

Sources & evidence

ORD record
ord-8c48d0a349c44351aa658559a7f46c54
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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