Boron tribromide → HCID 69131450, compound

HRID 349505Notes

Reaction equation

HRID 349505 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][N:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12]([C:14]2[C:22]3[N:21]=[C:20]([C:23]4[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][C:24]=4[CH2:30][CH2:31][N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)[NH:19][C:18]=3[C:17]([O:38]C)=[CH:16][CH:15]=2)=[O:13])[C:6]=1[Cl:7].B(Br)(Br)Br>O>[Cl:1][C:2]1[N:3]=[CH:4][N:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12]([C:14]2[C:22]3[N:21]=[C:20]([C:23]4[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][C:24]=4[CH2:30][CH2:31][N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)[NH:19][C:18]=3[C:17]([OH:38])=[CH:16][CH:15]=2)=[O:13])[C:6]=1[Cl:7]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69132695HCID 69132695, compound

Product 1

HCID 69131450HCID 69131450, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-[(2-morpholinoethyl)-4-amino-phenyl]-7-methoxy-1H-benzoimidazole-4-carboxylic acid-[3-(4,5-dichloro-imidazol-1-yl)-propyl]-amide (15 mg, 0.03 mmol) obtained in step 5 was dissolved in MC, BBr3 (1.0M solution in MC, 0.3 mL, 0.3 mmol) was added thereto and stirred at room temperature for 48 hours. The reaction was stopped by adding water thereto and the resulting solution was extracted with MC/MeOH (7:1). The extract was concentrated under a reduced pressure and purified by silica gel chromatography to obtain the title compound (5.9 mg, 0.01 mmol) in a yield of 40%.

Workup

  1. additionwas added
  2. extractionthe resulting solution was extracted with MC/MeOH (7:1)
  3. concentrationThe extract was concentrated under a reduced pressure
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-3e3a0e0ae6fd44de9f3868871629958b
Source dataset
uspto-grants-2007_02
Patent number
US07179832B2

Reaction notes

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