1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 52950484, compound

HRID 82928Notes

Reaction equation

HRID 82928 reaction equation
Cl.[O:2]=[C:3]1[NH:12][C:11]2[N:10]=[CH:9][C:8](/[CH:13]=[CH:14]/[C:15]([OH:17])=O)=[CH:7][C:6]=2[CH2:5][CH2:4]1.Cl.[NH:19]1[CH2:22][CH:21]([C:23]2[N:27]=[C:26]([CH3:28])[O:25][N:24]=2)[CH2:20]1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C>[CH3:28][C:26]1[O:25][N:24]=[C:23]([CH:21]2[CH2:22][N:19]([C:15](=[O:17])/[CH:14]=[CH:13]/[C:8]3[CH:7]=[C:6]4[C:11](=[N:10][CH:9]=3)[NH:12][C:3](=[O:2])[CH2:4][CH2:5]4)[CH2:20]2)[N:27]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 66905305(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid HydrochlorideHCID 67154694HCID 67154694, compound

Product 1

HCID 52950484HCID 52950484, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 16 mL vial flask was successively charged with (2E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride (30 mg, 0.12 mmol), DMF (3 mL), 3-azetidin-3-yl-5-methyl-1,2,4-oxadiazole hydrochloride (25 mg, 0.14 mmol; which may be prepared as described in Step 5), DIPEA (48 μL, 0.28 mmol) and EDAC (27 mg, 0.14 mmol). The reaction mixture was stirred at room temperature overnight and concentrated to dryness. The residue was purified on preparative TLC (eluent: dichloromethane/NH3 7N in MeOH, 2.5%) to give a white solid. This solid was triturated in acetone and diethyl ether, filtered, washed with acetone and diethyl ether then dried to give the title compound (23 mg, 56%) as a white solid.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was purified on preparative TLC (eluent: dichloromethane/NH3 7N in MeOH, 2.5%)
  3. customto give a white solid
  4. customThis solid was triturated in acetone
  5. filtrationdiethyl ether, filtered
  6. washwashed with acetone and diethyl ether
  7. customthen dried

Sources & evidence

ORD record
ord-6b29e02a50644155b3a155703e651271
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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