Triethylamine → HCID 70056819, compound

HRID 1029511Notes

Reaction equation

HRID 1029511 reaction equation
[F:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:20]([OH:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:22])=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:30][CH:31]([CH3:37])[CH2:32][CH2:33][C:34](Cl)=[O:35]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:30][CH:31]([CH3:37])[CH2:32][CH2:33][C:34]([O:22][CH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20](=[O:21])[N:12]1[C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[N:11][C:2]([F:1])=[CH:3][CH:4]=2)[N:9]=1)=[O:35]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 170008Pentanoyl chloride, 4-methyl-HCID 19900416HCID 19900416, compound

Product 1

HCID 70056819HCID 70056819, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The procedure is as in Example 7, but starting with 2-(7-fluoro-1,8-naphthyridin-2yl)-3-hydroxy-1-isoindolinone (5 g) in methylene chloride (60 cc), triethylamine (6.5 g), 4-methylpentanoyl chloride (3.66 g) and 4-dimethylaminopyridine (10 mg). After recrystallization in ethanol, 2-(7-fluoro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 4-methylpentanoate (1.2 g), m.p. 154° C., is obtained.

Workup

  1. customAfter recrystallization in ethanol

Sources & evidence

ORD record
ord-fff2068ac3374accbcd628db967af318
Source dataset
uspto-grants-1992_04
Patent number
US05102890

Reaction notes

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