1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 52950790, compound

HRID 83072Notes

Reaction equation

HRID 83072 reaction equation
Cl.[S:2]1[CH:6]=[C:5]([O:7][CH:8]2[CH2:11][NH:10][CH2:9]2)[C:4]2[CH:12]=[CH:13][CH:14]=[CH:15][C:3]1=2.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.Cl.[O:47]=[C:48]1[NH:57][C:56]2[N:55]=[CH:54][C:53](/[CH:58]=[CH:59]/[C:60](O)=[O:61])=[CH:52][C:51]=2[CH2:50][CH2:49]1>CN(C)C=O.O.C(OCC)(=O)C>[S:2]1[CH:6]=[C:5]([O:7][CH:8]2[CH2:11][N:10]([C:60](=[O:61])/[CH:59]=[CH:58]/[C:53]3[CH:52]=[C:51]4[C:56](=[N:55][CH:54]=3)[NH:57][C:48](=[O:47])[CH2:49][CH2:50]4)[CH2:9]2)[C:4]2[CH:12]=[CH:13][CH:14]=[CH:15][C:3]1=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 709268833-(Benzo[b]thiophen-3-yloxy)azetidine hydrochloride

Product 1

HCID 52950790HCID 52950790, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(benzo[b]thiophen-3-yloxy)azetidine hydrochloride (140 mg, 0.58 mmol), EDCI (111 mg, 0.48 mmol), HOBt (78 mg, 0.58 mmol) and diisopropylethylamine (420 μL, 2.41 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 (123 mg, 0.48 mmol) in dimethylformamide (10 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 (98:2 to 95:5) as eluent. The title product was obtained as a white solid (52 mg, 26%).

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-d0ee6df68d624ee2a35ca3e3b34f3be5
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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