1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 52950569, compound

HRID 633931Notes

Reaction equation

HRID 633931 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[C:14](=[O:15])[NH:13][C:12]2[N:11]=[CH:10][C:9](/[CH:16]=[CH:17]/[C:18]([OH:20])=O)=[CH:8][C:7]=2[CH2:6]1)=[O:4].Cl.[F:22][C:23]1[CH:36]=[CH:35][C:26]([O:27][CH2:28][CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:25][CH:24]=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[F:22][C:23]1[CH:24]=[CH:25][C:26]([O:27][CH2:28][CH:29]2[CH2:30][CH2:31][N:32]([C:18](=[O:20])/[CH:17]=[CH:16]/[C:9]3[CH:8]=[C:7]4[C:12](=[N:11][CH:10]=3)[NH:13][C:14](=[O:15])[CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6]4)[CH2:33][CH2:34]2)=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 172028284-[(4-Fluorophenoxy)methyl]piperidine hydrochlorideHCID 67154711(2E)-3-[6-(Methoxycarbonyl)-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl]acrylic acid

Product 1

HCID 52950569HCID 52950569, compoundYield 9.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2E)-3-[6-(methoxycarbonyl)-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl]acrylic acid (96 mg, 0.35 mmol; which may be prepared as described in Step 4) in DMF (8 mL) were added 4-[(4-fluorophenoxy)methyl]piperidine hydrochloride (102 mg, 0.42 mmol; which may be prepared as described in Step 2), DIPEA (144 μL, 0.83 mmol), 4-DMAP (17 mg, 0.14 mmol) and EDAC (80 mg, 0.42 mmol). The reaction mixture was stirred at room temperature overnight and concentrated to dryness. The residue was purified by flash chromatography on silica gel (eluent: dichloromethane/MeOH from 100/0 to 80/20) to give a first solid which is purified again on preparative TLC (eluent: dichloromethane/MeOH 95/5) to give the title compound (15 mg, 8%) as a white solid.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was purified by flash chromatography on silica gel (eluent: dichloromethane/MeOH from 100/0 to 80/20)
  3. customto give a first solid which
  4. customis purified again on preparative TLC (eluent: dichloromethane/MeOH 95/5)

Sources & evidence

ORD record
ord-7936a44c5af84ae89342b4b9204b145b
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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