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

HRID 82975Notes

Reaction equation

HRID 82975 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-228217ee1c5f4f1a83478d192281aeaa
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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