1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 52950791, compound

HRID 83075Notes

Reaction equation

HRID 83075 reaction equation
Cl.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[S:7][CH:8]1[CH2:11][NH:10][CH2:9]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>[O:57]=[C:56]([N:10]1[CH2:11][CH:8]([S:7][C:3]2[S:2][CH:6]=[CH:5][CH:4]=2)[CH2:9]1)/[CH:55]=[CH:54]/[C:49]1[CH:48]=[C:47]2[C:52](=[N:51][CH:50]=1)[NH:53][C:44](=[O:43])[CH2:45][CH2:46]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 671545453-(Thiophen-2-ylthio)-azetidine hydrochloride

Product 1

HCID 52950791HCID 52950791, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(Thiophen-2-ylthio)-azetidine hydrochloride (170 mg, 0.82 mmol), EDCI (157 mg, 0.82 mmol), HOBt (110 mg, 0.82 mmol) and diisopropylethylamine (240 μL, 1.36 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 (139 mg, 0.55 mmol) in dimethylformamide (14 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 petroleum ether/ethyl acetate (1:0 to 95:5) as eluent. After trituration in acetone, the title product was obtained as a white solid (114 mg, 37%).

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

Sources & evidence

ORD record
ord-aacc13f622c24d40a07e35f90df44b96
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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