Boron tribromide → HCID 22346418, compound

HRID 897322Notes

Reaction equation

HRID 897322 reaction equation
[CH3:1][N:2]([CH3:30])[C:3]([N:5]([CH3:29])[C:6]1[N:15]=[C:14]([C:16]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[O:17])[C:13]([O:27]C)=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2)=[O:4].B(Br)(Br)Br>C(Cl)Cl>[CH3:1][N:2]([CH3:30])[C:3]([N:5]([CH3:29])[C:6]1[N:15]=[C:14]([C:16]([NH:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)=[O:17])[C:13]([OH:27])=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2)=[O:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22346324HCID 22346324, compound

Product 1

HCID 22346418HCID 22346418, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-[[(dimethylamino)carbonyl](methyl)amino]-N-(4-fluorobenzyl)-8-methoxy-1,6-naphthyridine-7-carboxamide from step 2 in CH2Cl2 (1 mL) at −78 C was added boron tribromide (0.10 mL of a 1M solution in CH2Cl2, 0.01 mmol). The reaction was allowed to warm to room temperature and stirred an additional 16 hr. The solvent was evaporated in vacuo and the residue dissolved in MeOH (2 mL) and the solvent again evaporated in vacuo. The residue was dissolved in DMF (1 mL) and purified by reverse phase HPLC. (Vydak C18, Gradient elution with Water:Acetonitrile 95:5 to 5:95 with 0.1% TFA at 30 mL/min over 15 mins). Lyophilization of the pure fractions afforded the title compound as an off white solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue dissolved in MeOH (2 mL)
  3. customthe solvent again evaporated in vacuo
  4. dissolutionThe residue was dissolved in DMF (1 mL)
  5. custompurified by reverse phase HPLC
  6. wash(Vydak C18, Gradient elution with Water:Acetonitrile 95:5 to 5:95 with 0.1% TFA at 30 mL/min over 15 mins)

Sources & evidence

ORD record
ord-73197100555e43f8abb7458dc5f97c69
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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