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

HRID 2172127Notes

Reaction equation

HRID 2172127 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-115a254d524041ef8aae574184968402
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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