Triethylamine → HCID 19900402, compound

HRID 1029507Notes

Reaction equation

HRID 1029507 reaction equation
[OH:1][CH:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N: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(N(CC)CC)C.[C:30](Cl)(=[O:34])[CH:31]([CH3:33])[CH3:32]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:30]([O:11][CH:4]1[C:5]2[C:10](=[N:9][CH:8]=[CH:7][N:6]=2)[C:2](=[O:1])[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:34])[CH:31]([CH3:33])[CH3:32]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 64531286-(7-chloro-1,8-naphthyridin-2-yl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one

Product 1

HCID 19900402HCID 19900402, compoundYield 29.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The procedure is as in Example 7, but starting with 5-hydroxy-6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine (6.3 g) in methylene chloride (80 cc), triethylamine (5.05 g), isobutyryl chloride (4.25 g) and 4-dimethylaminopyridine (50 mg). The solid obtained is washed with tetrahydrofuran. 6-(7-Chloro-1,8-naphthyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl isobutyrate (2.3 g), m.p. 260°-262° C., is thereby obtained.

Workup

  1. customThe solid obtained
  2. washis washed with tetrahydrofuran

Sources & evidence

ORD record
ord-3122dda8cc95458ca1c17d4a5d7cdda1
Source dataset
uspto-grants-1992_04
Patent number
US05102890

Reaction notes

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