Water → HCID 59007071, compound

HRID 130454Notes

Reaction equation

HRID 130454 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[CH:11][C:12]([O:30]C)=[C:13]([NH:15][S:16]([C:19]3[S:20][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)=[CH:22][CH:23]=3)(=[O:18])=[O:17])[CH:14]=2)[CH2:3]1.B(Br)(Br)Br.O.C(=O)(O)[O-].[Na+]>ClCCl.CO>[CH3:8][C@H:6]1[NH:7][C@@H:2]([CH3:1])[CH2:3][N:4]([C:9]2[CH:10]=[CH:11][C:12]([OH:30])=[C:13]([NH:15][S:16]([C:19]3[S:20][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)=[CH:22][CH:23]=3)(=[O:18])=[O:17])[CH:14]=2)[CH2:5]1

Participants

7

Reactant 4

HCID 962WaterHCID 25134Boron tribromide2×HCID 516892Sodium BicarbonateHCID 11525404HCID 11525404, compound

Product 1

HCID 59007071HCID 59007071, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent3×

Procedure

N-[5-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-5-(2-pyridinyl)-2-thiophenesulfonamide (E13) (277 mg, 0.66 mmol) was dissolved in dichloromethane (5 ml) and treated with 1M boron tribromide in dichloromethane (1.8 ml, 1.8 mol) for 4.5 hours. Further 1M boron tribromide in dichloromethane (3 ml, 3 mmol) was added and the mixture stirred at room temperature overnight. Water and methanol were cautiously added and the solution basified to pH9 with saturated aqueous sodium bicarbonate solution. The precipitated solids were filtered, washed with ether and purified by mass directed autoprep HPLC to afford the title compound (E120). MS (ES+) m/e 445 [M+H]+.

Workup

  1. filtrationThe precipitated solids were filtered
  2. washwashed with ether
  3. custompurified by mass

Sources & evidence

ORD record
ord-7e89c030ebf149c79f41b174a52994dc
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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