Dimethyl Sulfoxide → 4-[7-(3-Piperidin-1-yl-propoxy)-3,4-dihydro-1H-isoquinoline-2-sulfonyl]-benzamide

HRID 2250126Notes

Reaction equation

HRID 2250126 reaction equation
CS(C)=[O:3].C([O-])([O-])=O.[K+].[K+].[C:11]([C:13]1[CH:18]=[CH:17][C:16]([S:19]([N:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][C:26]([O:32][CH2:33][CH2:34][CH2:35][N:36]4[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]4)=[CH:27][CH:28]=3)[CH2:23]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1)#[N:12].OO>CO.O>[N:36]1([CH2:35][CH2:34][CH2:33][O:32][C:26]2[CH:25]=[C:24]3[C:29]([CH2:30][CH2:31][N:22]([S:19]([C:16]4[CH:17]=[CH:18][C:13]([C:11]([NH2:12])=[O:3])=[CH:14][CH:15]=4)(=[O:20])=[O:21])[CH2:23]3)=[CH:28][CH:27]=2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 59640602HCID 59640602, compound

Product 1

HCID 596404364-[7-(3-Piperidin-1-yl-propoxy)-3,4-dihydro-1H-isoquinoline-2-sulfonyl]-benzamideYield 26%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A 1.4 mL DMSO mixture of K2CO3 is stirred under N2, 2-(4-cyanobenzenesulfonyl)-7-(3-piperidin-1-yl-propoxy)-1,2,3,4-tetrahydro-isoquinoline (75 mg, 0.17 mmol) is added, 0.2 mL H2O added, followed by 30% H2O2 (1.4 mL, 12 mmol) and reaction is stirred at room temperature for 4 hours. The reaction mixture is diluted with MeOH, filtered, and the solids washed twice with MeOH. The filtrate is concentrated and the residue is purified by chromatography (SCX-MeOH wash, elute 2M NH3/MeOH; then SiO2; 0-10% MeOH/CH2Cl2/1% NH4OH gradient) to give the product as an off-white solid (26 mg, 26% yld). MS (ES+)458.2(M+H)+.

Workup

  1. stirringis stirred at room temperature for 4 hours
  2. filtrationfiltered
  3. washthe solids washed twice with MeOH
  4. concentrationThe filtrate is concentrated
  5. customthe residue is purified by chromatography (SCX-MeOH
  6. washwash
  7. washelute 2M NH3/MeOH

Sources & evidence

ORD record
ord-45fb2946934b4d6cbf2f24fd4527c789
Source dataset
uspto-grants-2008_01
Patent number
US07314937B2

Reaction notes

Loading…