Boron tribromide → HCID 10299465, compound

HRID 897324Notes

Reaction equation

HRID 897324 reaction equation
[F:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[N:24]([CH3:25])[C:23](=[O:26])[N:22]([CH2:27][CH2:28][N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)[C:14]4=[CH:15][CH:16]=[N:17][C:18]([C:19]=2[O:20]C)=[C:13]34)=[O:9])=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[N:24]([CH3:25])[C:23](=[O:26])[N:22]([CH2:27][CH2:28][N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)[C:14]4=[CH:15][CH:16]=[N:17][C:18]([C:19]=2[OH:20])=[C:13]34)=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22346264HCID 22346264, compound

Product 1

HCID 10299465HCID 10299465, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(4-fluorobenzyl)-6-methoxy-3-methyl-1-(2-morpholin-4-ylethyl)-2-oxo-2,3-dihydro-1H-pyrimido[4,5,6-de]-1,6-naphthyridine-5-carboxamide from step 1 (0.038 g, 0.077 mmol) in CH2Cl2 (1 mL) at −78 C was added boron tribromide (0.077 mL of a 1M solution in CH2Cl2, 0.077 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 methanol (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 methanol (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-f3ad9563ee08470292e2dd16102ee705
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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