Boron tribromide → HCID 178484079, compound

HRID 491770Notes

Reaction equation

HRID 491770 reaction equation
[CH3:1][N:2]([CH3:33])[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([NH:11][C:12]2[C:16]3[CH:17]=[CH:18][C:19]([O:21]C)=[CH:20][C:15]=3[O:14][C:13]=2[C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][N:27]=2)=[O:24])=[O:10])[CH2:5][CH2:4]1.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[CH3:1][N:2]([CH3:33])[C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([NH:11][C:12]2[C:16]3[CH:17]=[CH:18][C:19]([OH:21])=[CH:20][C:15]=3[O:14][C:13]=2[C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][N:27]=2)=[O:24])=[O:10])[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 178487636HCID 178487636, compound

Product 1

HCID 178484079HCID 178484079, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of trans-3-[4-(dimethylamino)cyclohexylcarbonylamino]-6-methoxy-N-(5-chloropyridin-2-yl)-benzofuran-2-carboxamide (473 mg) obtained in Example 23 in dichloromethane (20 ml) is added dropwise boron tribromide (3.5 g) over 2 minutes at −78° C. The mixture is stirred at room temperature for 4 days, and the reaction solution is poured into ice-water, neutralized with a saturated aqueous sodium hydrogen carbonate solution, and extracted with a mixed solvent of ethyl acetate-tetrahydrofuran. The organic layer is washed with a saturated brine, dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The resulting residue is suspended in chloroform/diethyl ether, and the precipitates are collected by filtration, and dried to give trans-3-[4-(dimethylamino)cyclohexylcarbonylamino]-6-hydroxy-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (335 mg). This product (48 mg) is suspended in methanol and treated with 4N hydrogen chloride in dioxane to give the title compound (54 mg).

Workup

  1. extractionextracted with a mixed solvent of ethyl acetate-tetrahydrofuran
  2. washThe organic layer is washed with a saturated brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent is evaporated under reduced pressure
  5. filtrationthe precipitates are collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-b4bcf2e074134958aee4ea7747c02095
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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