Cyclohexylamine → HCID 18549174, compound

HRID 1266178Notes

Reaction equation

HRID 1266178 reaction equation
[F:1][C:2]1[C:22](F)=[CH:21][C:5]2=[N:6][C:7]3[N:8]([CH3:20])[CH:9]=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:11](=[O:14])[C:12]=3[CH:13]=[C:4]2[CH:3]=1.[CH:24]1([NH2:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>CS(C)=O>[CH:24]1([NH:30][C:22]2[C:2]([F:1])=[CH:3][C:4]3[C:5]([CH:21]=2)=[N:6][C:7]2[N:8]([CH3:20])[CH:9]=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:11](=[O:14])[C:12]=2[CH:13]=3)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 98399873-Ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

Product 1

HCID 18549174HCID 18549174, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Ethyl 8-cyclohexylamino-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate was prepared under the conditions of Example 4, but from 3 g of ethyl 7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate and 2.2 cm3 of cyclohexylamine in 30 cm3 of dimethyl sulphoxide. After filtering 2 times with 15 cm3 of ethanol, 3.3 g of ethyl 8-cyclohexylamino-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate were obtained in the form of a yellow solid melting at about 220° C.

Workup

  1. customEthyl 8-cyclohexylamino-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate was prepared under the conditions of Example 4
  2. filtrationAfter filtering 2 times with 15 cm3 of ethanol

Sources & evidence

ORD record
ord-46c287f9dd734891a7be4858301db08c
Source dataset
uspto-grants-2003_04
Patent number
US06548506B2

Reaction notes

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