1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 52950613, compound

HRID 2172043Notes

Reaction equation

HRID 2172043 reaction equation
Cl.[CH3:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[CH2:8][O:9][CH:10]1[CH2:13][NH:12][CH2:11]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.Cl.[O:45]=[C:46]1[NH:55][C:54]2[N:53]=[CH:52][C:51](/[CH:56]=[CH:57]/[C:58](O)=[O:59])=[CH:50][C:49]=2[CH2:48][CH2:47]1>CN(C)C=O>[CH3:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[CH2:8][O:9][CH:10]1[CH2:11][N:12]([C:58](=[O:59])/[CH:57]=[CH:56]/[C:51]2[CH:50]=[C:49]3[C:54](=[N:53][CH:52]=2)[NH:55][C:46](=[O:45])[CH2:47][CH2:48]3)[CH2:13]1

Participants

7

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 67154572HCID 67154572, compound

Product 1

HCID 52950613HCID 52950613, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-((3-methylthiophen-2-yl)methoxy)azetidine hydrochloride (129.0 mg, 0.6 mmol), EDCI (112.0 mg, 0.6 mmol), HOBt (82.0 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 (100.0 mg, 0.4 mmol) in dimethylformamide (10 mL) at room temperature. The reaction mixture was stirred overnight and then partitioned between ethyl acetate (30 mL) and water (30 mL). The aqueous layer was separated and extracted with ethyl acetate (2×20 mL). The combined organic phases were washed with a saturated solution of sodium chloride (3×30 mL), dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel, using dichloromethane/methanol (100:0 to 95:5) as eluent. The residue was triturated in acetone to give a white solid (66.0 mg, 44%).

Workup

  1. custompartitioned between ethyl acetate (30 mL) and water (30 mL)
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (2×20 mL)
  4. washThe combined organic phases were washed with a saturated solution of sodium chloride (3×30 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by chromatography on silica gel
  9. customThe residue was triturated in acetone

Sources & evidence

ORD record
ord-4802d2bafa31416191e4c047c75d75df
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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