Sodium Chloride → HCID 135433064, compound

HRID 719204Notes

Reaction equation

HRID 719204 reaction equation
[CH3:1][N:2]([CH3:30])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:21]2[C:12](=[N:13][C:14]3[C:19]([N:20]=2)=[C:18]2[CH:22]=[CH:23][CH:24]=[C:25]([O:26][CH3:27])[C:17]2=[CH:16][CH:15]=3)[CH:11]=[CH:10][C:9]=1[O:28]C)=[O:7].B(Br)(Br)Br.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Na+]>ClCCl>[CH3:30][N:2]([CH3:1])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:21]2[C:12](=[N:13][C:14]3[C:19]([N:20]=2)=[C:18]2[CH:22]=[CH:23][CH:24]=[C:25]([O:26][CH3:27])[C:17]2=[CH:16][CH:15]=3)[CH:11]=[CH:10][C:9]=1[OH:28])=[O:7]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 10179363HCID 10179363, compound

Product 1

HCID 135433064HCID 135433064, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold solution of 4,10-dimethoxy-benzo[a]phenazine-11-carboxylic acid (2-dimethylamino-ethyl)-amide (300 mg) in dichloromethane (25 mL) was added a 1.0M solution of boron tribromide in dichloromethane (1.63 mL, 2.2 equivalents). The reaction mixture was stirred for 6 hours and then ice was added with sodium carbonate and sodium chloride. The organics were extracted into dichloromethane, dried (MgSO4), and the solvent removed in vacuo to yield a yellow solid which was purified using flash chromatography to yield the title compound (61 mg)

Workup

  1. extractionThe organics were extracted into dichloromethane
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customto yield a yellow solid which
  5. customwas purified

Sources & evidence

ORD record
ord-4adb6ecaf2254527a198a9e2c45290de
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

Loading…