1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86745636, compound

HRID 1029510Notes

Reaction equation

HRID 1029510 reaction equation
Cl[CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[N:15][C:16]([Cl:22])=[CH:17][CH:18]=2)[N:13]=1.[CH3:23][N:24]([CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[C:25](=[O:27])[CH3:26].N12CCCN=C1CCCCC2>CN(C)C=O>[CH3:23][N:24]([CH2:28][CH2:29][CH2:30][C:31]([O:33][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[N:15][C:16]([Cl:22])=[CH:17][CH:18]=2)[N:13]=1)=[O:32])[C:25](=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinoneHCID 19900399HCID 19900399, compound

Product 1

HCID 86745636HCID 86745636, compoundYield 22.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The procedure is as in Example 1, but starting with 3-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (9.9 g) in anhydrous dimethylformamide (100 cc), 4-(N-methylacetamido)butanoic acid (4.8 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (4.6 g). The oily residue obtained is purified by chromatography on silica (0.063-0.2 mm; 150 g) contained in a column 3 cm in diameter [eluant: methylene chloride/methanol (99:1 by volume)] and collecting 30-cc fractions. Fractions 76 to 175 are concentrated to dryness under reduced pressure (2.7 kPa) at 60° C. and, after crystallization in ethyl ether, 2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 4-(N-methylacetamido)butyrate (3.1 g), m.p. 170° C., is obtained.

Workup

  1. customThe oily residue obtained
  2. customis purified by chromatography on silica (0.063-0.2 mm; 150 g)
  3. customcollecting 30-cc fractions
  4. concentrationFractions 76 to 175 are concentrated to dryness under reduced pressure (2.7 kPa) at 60° C.
  5. customafter crystallization in ethyl ether

Sources & evidence

ORD record
ord-2f92b7a00eda4200955565d53bedc01c
Source dataset
uspto-grants-1992_04
Patent number
US05102890

Reaction notes

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