Diethyl Ether → HCID 54707855, compound

HRID 1817362Notes

Reaction equation

HRID 1817362 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[F:30])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:24]C)[C:10](=[O:23])[N:11]([CH3:22])[C:12]=2[N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])[C:7]1=[O:26].C(OCC)C>Br.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[F:30])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:24])[C:10](=[O:23])[N:11]([CH3:22])[C:12]=2[N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])[C:7]1=[O:26]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 69061292HCID 69061292, compound

Product 1

HCID 54707855HCID 54707855, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution of N-[6-(3-chloro-4-fluorobenzyl)-4-methoxy-2-methyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridin-1-yl]-N-methylmethane-sulfonamide (48 mg, 0.11 mmol) in 33% HBr in acetic acid (1 mL) was heated in an oil bath at 50° C. for 15 minutes. The product mixture was concentrated under vacuum, and the residue subject to preparative reverse phase HPLC purification. Collection and lyophilization of appropriate fractions afforded an oil. Trituration of the residual oil with diethyl ether provided the title compound as off white solid.

Workup

  1. concentrationThe product mixture was concentrated under vacuum
  2. customthe residue subject to preparative reverse phase HPLC purification
  3. customCollection and lyophilization of appropriate fractions
  4. customafforded an oil

Sources & evidence

ORD record
ord-f3c5f2f342b94172ae1f789582160ad6
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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