1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86745628, compound

HRID 1029496Notes

Reaction equation

HRID 1029496 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.[C:23]([NH:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])(=[O:27])[CH:24]([CH3:26])[CH3:25].N12CCCN=C1CCCCC2>CN(C)C=O>[C:23]([NH:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][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:33])(=[O:27])[CH:24]([CH3:26])[CH3:25]

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 16772272HCID 16772272, compound

Product 1

HCID 86745628HCID 86745628, compoundYield 39.3%

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-isobutyrylaminobutyric acid (5.2 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (4.6 g). The residue obtained is recrystallized in acetonitrile and then purified by chromatography on silica (0.063-0.2 mm; 130 g) contained in a column 3 cm in diameter [eluant: methylene chloride/methanol (98:2 by volume) mixture] collecting 25-cc fractions. Fractions 79 to 85 are combined and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is crystallized by stirring in isopropyl ether. 2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 4-isobutyrylaminobutyrate (5.5 g), m.p. 208° C., is thereby obtained.

Workup

  1. customThe residue obtained
  2. customis recrystallized in acetonitrile
  3. custompurified by chromatography on silica (0.063-0.2 mm; 130 g)
  4. customcollecting 25-cc fractions
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue obtained
  7. customis crystallized

Sources & evidence

ORD record
ord-95c975fad2c44abcbe02228a18c98f98
Source dataset
uspto-grants-1992_04
Patent number
US05102890

Reaction notes

Loading…