Sodium Chloride → HCID 178483823, compound

HRID 719203Notes

Reaction equation

HRID 719203 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]C)[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>[CH3:1][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]([OH:26])[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 178483823HCID 178483823, compoundYield 6.7%

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 (96 mg) in dichloromethane (2 mL) was added a 11.0M solution of boron tribromide in dichloromethane (2.14 mL, 9 equivalents). The reaction mixture was stirred for 16 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 an orange compound which was recrystallised from dichloromethane/methanol/hexane to yield the title compound (6 mg).

Workup

  1. extractionThe organics were extracted into dichloromethane
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customto yield an orange compound which
  5. customwas recrystallised from dichloromethane/methanol/hexane

Sources & evidence

ORD record
ord-bc3bc5d63b3e4cd2a654e31c4017221e
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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