Potassium Phosphate, Tribasic → HCID 24855059, compound

HRID 79096Notes

Reaction equation

HRID 79096 reaction equation
Br[C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13]([NH2:16])(=[O:15])=[O:14])[CH:8]=1)=[O:5].[N:21]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[OH:33])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.O.[Cu]I>[N:21]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][C:2]2[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=2[C:4]([NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([S:13]([NH2:16])(=[O:15])=[O:14])[CH:8]=2)=[O:5])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 32622502-(Piperidin-1-yl)phenolHCID 265805112-bromo-N-(3-(aminosulfonyl)phenyl)benzamide

Product 1

HCID 24855059HCID 24855059, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 2-bromo-N-(3-(aminosulfonyl)phenyl)benzamide (0.10 g, 0.28 mmol), 2-(piperidin-1-yl)phenol (74 mg, 0.28 mmol), K3PO4 (0.12 g, 0.56 mmol), and CuI (53 mg, 0.28 mmol) in DMF (1 mL) and water (20 μL) was sealed in a glass tube and heated in a microwave oven at 150° C. for 15 min. The reaction was filtered and purified by preparative reverse phase HPLC using 10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA) to give 2-(2-(piperidin-1-yl)phenoxy)-N-(3-(aminosulfonyl)phenyl)benzamide. LC/MS: m/z 452.0 (M+H)+ at 2.31 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customwas sealed in a glass tube
  2. filtrationThe reaction was filtered
  3. custompurified by preparative reverse phase

Sources & evidence

ORD record
ord-8ff2be434a974ceb848b4bf55ae14d5c
Source dataset
uspto-grants-2014_09
Patent number
US08841483B2

Reaction notes

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