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Diisopropyl Ether → HCID 86745629, compound

HRID 1029497
Notes
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Reaction equation

HRID 1029497 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]([N:28]1[CH2:33][CH2:32][CH:31]([C:34]([OH:36])=[O:35])[CH2:30][CH2:29]1)(=[O:27])[CH2:24][CH2:25][CH3:26].N12CCCN=C1CCCCC2.C(OC(C)C)(C)C>CN(C)C=O>[C:23]([N:28]1[CH2:29][CH2:30][CH:31]([C:34]([O:36][CH:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4](=[O:11])[N:3]2[C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[N:15][C:16]([Cl:22])=[CH:17][CH:18]=3)[N:13]=2)=[O:35])[CH2:32][CH2:33]1)(=[O:27])[CH2:24][CH2:25][CH3:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7914Diisopropyl EtherHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinoneHCID 199004171-(1-Oxobutyl)-4-piperidinecarboxylic acid

Product 1

HCID 86745629HCID 86745629, compoundYield 40.6%

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), 1-butyryl-4-piperidinecarboxylic acid (6 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (4.6 g). The residue obtained is purified by chromatography on silica (0.063-0.2 mm; 250 g) contained in a column 4.2 cm in diameter [eluant: a mixture of methylene chloride and methanol (99:1 by volume)], collecting 70-cc fractions. Fractions 82 to 110 are combined and concentrated to dryness under reduced pressure (b 2.7 kPa). The solid obtained is taken up with stirring with isopropyl ether, then separated by filtration and dried. 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 1-butyryl-4-piperidinecarboxylate (6 g), m.p. 165° C., is thereby obtained.

Workup

  1. customThe residue obtained
  2. customis purified by chromatography on silica (0.063-0.2 mm; 250 g)
  3. additiona mixture of methylene chloride and methanol (99:1 by volume)],
  4. customcollecting 70-cc fractions
  5. concentrationconcentrated to dryness under reduced pressure (b 2.7 kPa)
  6. customThe solid obtained
  7. customseparated by filtration
  8. customdried

Sources & evidence

ORD record
ord-a06013534be048ab9f8893e57a3f2b94
Source dataset
uspto-grants-1992_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05102890

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes