3-Amino-1,2,4-triazine → HCID 20071616, compound

HRID 1073590Notes

Reaction equation

Cl[C:2]1[C:11]([C:12]([C:14](=[CH:20][N:21](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]([Cl:25])=[C:7]([F:24])[CH:8]=2)[N:3]=1.NC1N=NC=CN=1>ClC(Cl)Cl>[Cl:25][C:6]1[C:7]([F:24])=[CH:8][C:9]2[C:4]([CH:5]=1)=[N:3][C:2]1[NH:21][CH:20]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:12](=[O:13])[C:11]=1[CH:10]=2

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 11.3 g of ethyl 2-(2,7,-dichloro-6-fluoroquinoline-3-carbonyl)-3-dimethylaminoacrylate and 5.65 g of 3-amino-1,2,4-triazine in 60 cm3 of trichloromethane is stirred for 16 hours at a temperature close to 20 C. The reaction mixture is concentrated to dryness under reduced pressure (20 kPa) at a temperature close to 30° C. The residue is taken up in 60 cm3 of ethanol and 5.6 g of DBU and the mixture is heated at a temperature close to 75° C. for 20 hours. After cooling to 20° C., the insoluble matter is drained and washed with twice 40 cm3 of ethanol. 6.1 g of 8-chloro-3-ethoxycarbonyl-7-fluoro-4-oxo-1,4-dihydrobenzo [b][1,8]naphthyridine are obtained in the form of a brown solid which decomposes at 378°-380° C. and which can be used for the subsequent steps without further purification.

Workup

customclose to 20 C
concentrationThe reaction mixture is concentrated to dryness under reduced pressure (20 kPa) at a temperature
customclose to 30° C
temperature5.6 g of DBU and the mixture is heated at a temperature
customclose to 75° C. for 20 hours
washwashed with twice 40 cm3 of ethanol

Sources & evidence

ORD record: ord-4170da5a9c3d47748767f4d8243d989c
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04970213

Reaction notes

Loading…