Pyrrolidone carboxylic acid → HCID 86745625, compound

HRID 1029487Notes

Reaction equation

HRID 1029487 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.[NH:23]1[C:27](=[O:28])[CH2:26][CH2:25][CH:24]1[C:29]([OH:31])=[O:30].N12CCCN=C1CCCCC2>CN(C)C=O>[O:28]=[C:27]1[NH:23][CH:24]([C:29]([O:31][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:30])[CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 499Pyrrolidone carboxylic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone

Product 1

HCID 86745625HCID 86745625, compoundYield 69.4%

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), DL-pyroglutamic acid (3.9 g) and 1,8-diazabicyclo[5.4.0]-undec-7ene (4.6 g). After recrystallization in dimethylformamide, 2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 5-oxo-2-pyrrolidinecarboxylate (8.8 g), m.p. 255° C. (decomposition), is obtained.

Workup

  1. customAfter recrystallization in dimethylformamide

Sources & evidence

ORD record
ord-a7ca0eb02a0b4f7ab1ba22dfee084a7d
Source dataset
uspto-grants-1992_04
Patent number
US05102890

Reaction notes

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