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

HRID 2171984Notes

Reaction equation

HRID 2171984 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-a706d3ec8be8491796615759fc39d95c
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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