Dimethylformamide → HCID 86745633, compound

HRID 1029504Notes

Reaction equation

HRID 1029504 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](C3C4C(=CC=CC=4)C(=O)N3)=[N:9]2)=[CH:4][CH:3]=1.[O:22]=[C:23]1[CH2:28][CH2:27][CH:26]([C:29]([OH:31])=[O:30])[CH2:25][CH2:24]1.N12[CH2:42][CH2:41][CH2:40][N:39]=[C:38]1[CH2:37][CH2:36][CH2:35][CH2:34]C2.CN(C)C=[O:46]>>[O:22]=[C:23]1[CH2:28][CH2:27][CH:26]([C:29]([O:31][CH:40]2[C:41]3[C:37](=[CH:36][CH:35]=[CH:34][CH:42]=3)[C:38](=[O:46])[N:39]2[C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[N:11][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=2)=[O:30])[CH2:25][CH2:24]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1927304-Oxocyclohexanecarboxylic acidHCID 19900451HCID 19900451, compound

Product 1

HCID 86745633HCID 86745633, compound

Procedure

The procedure is as in Example 1, but starting with 3-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (9.9 g) in anhydrous dimethylformamide (100 cc), 4-oxocyclohexanecarboxylic acid (4.25 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (4.6 g). After recrystallization in acetonitrile, 2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 4-oxocyclohexanecarboxylate (8.5 g), m.p. 203° C., is obtained.

Workup

  1. customAfter recrystallization in acetonitrile

Sources & evidence

ORD record
ord-1084efbeb45649559c8a6e042a90b8c3
Source dataset
uspto-grants-1992_04
Patent number
US05102890

Reaction notes

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