Boron tribromide → HCID 54698647, compound

HRID 1817352Notes

Reaction equation

HRID 1817352 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:29]C)[C:10](=[O:28])[N:11]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)[C:12]=2[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[C:7]1=[O:31].B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:29])[C:10](=[O:28])[N:11]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)[C:12]=2[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[C:7]1=[O:31]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69060904HCID 69060904, compound

Product 1

HCID 54698647HCID 54698647, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6-(3-chloro-4-fluorobenzyl)-4-methoxy-N,N-dimethyl-2-(4-methyl-phenyl)-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide (0.054 g, 0.108 mmol) in anhydrous dichloromethane (10 mL) was treated with a solution of boron tribromide (0.3 mL, 1M) in dichloromethane. The reaction mixture was stirred at room temperature for 3 hours. The product mixture was concentrated under vacuum, and the residue subject to preparative reverse phase HPLC purification. Collection and lyophilization of appropriate fractions provide the titled compound.

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

Sources & evidence

ORD record
ord-4c23c2c8893a455a86626c93d3a97a42
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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