Tert-Butylamine → 3-Ethoxycarbonyl-7,8-difluoro-4-oxo-1-tert-butyl-1,4dihydrobenzo[b][1,8]naphthyridine

HRID 743647Notes

Reaction equation

HRID 743647 reaction equation
Cl[C:2]1[C:11]([C:12]([C:14](=[CH:20]N(C)C)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:25])=[C:7]([F:24])[CH:8]=2)[N:3]=1.[C:26]([NH2:30])([CH3:29])([CH3:28])[CH3:27]>>[CH2:18]([O:17][C:15]([C:14]1[C:12](=[O:13])[C:11]2[CH:10]=[C:9]3[CH:8]=[C:7]([F:24])[C:6]([F:25])=[CH:5][C:4]3=[N:3][C:2]=2[N:30]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:20]=1)=[O:16])[CH3:19]

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 53731972Ethyl 2-(2-chloro-6,7-difluoroquinoline-3-carbonyl)-3-dimethylaminoacrylate

Product 1

HCID 194236303-Ethoxycarbonyl-7,8-difluoro-4-oxo-1-tert-butyl-1,4dihydrobenzo[b][1,8]naphthyridineYield 69.1%

Procedure

3-Ethoxycarbonyl-7,8-difluoro-4-oxo-1-tert-butyl-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions described in Example 10, but starting with 4 g of ethyl 2-(2-chloro-6,7-difluoro-3-quinolylcarbonyl)-3(dimethylamino)acrylate and 0.87 g of tert-butylamine. 2.7 g of 3-ethoxycarbonyl-7,8-difluoro-4-oxo-1-tert-butyl-1,4dihydrobenzo[b][1,8]naphthyridine are obtained in the form of a yellow solid, melting point 206° C., which is used without further purification for the subsequent steps.

Workup

  1. custom3-Ethoxycarbonyl-7,8-difluoro-4-oxo-1-tert-butyl-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions

Sources & evidence

ORD record
ord-98f60e514c7f419293c64d5fa5bd3319
Source dataset
uspto-grants-1996_09
Patent number
US05556861

Reaction notes

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