Hexane → Methyl 6-(3-chloro-4-fluorobenzyl)-4-methoxy-2-[4-(methylamino)butyl]-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate

HRID 2426451Notes

Reaction equation

HRID 2426451 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:27])[C:10](=[O:26])[N:11]([CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH3:25])[C:12]=2[C:16]([O:18][CH3:19])=[O:17])[C:7]1=[O:28].[CH3:33][Si](C=[N+]=[N-])(C)C.CCCCCC>ClCCl.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:27][CH3:33])[C:10](=[O:26])[N:11]([CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH3:25])[C:12]=2[C:16]([O:18][CH3:19])=[O:17])[C:7]1=[O:28]

Participants

5

Reactant 3

HCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 66997664Methyl 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-2-[4-(methylamino)butyl]-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate

Product 1

HCID 66997854Methyl 6-(3-chloro-4-fluorobenzyl)-4-methoxy-2-[4-(methylamino)butyl]-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of methyl 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-2-[4-(methylamino)butyl]-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate (0.68 g, 1.45 mmol; Example 1, Step 11) and a solution of trimethylsilyldiazomethane in hexane (2.2 mL, 4.35 mmol; 2M) in dichloromethane-methanol (1.5 & 4.5 mL) was stirred at room temperature for one hour. The reaction mixture was concentrated under vacuum to provide the title compound. This was used in the following step without further purification. ES MS M+1=480

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-0091745fbd384accad5ce20dd1c832f3
Source dataset
uspto-grants-2011_06
Patent number
US07968564B2

Reaction notes

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