HCID 10531590, compound → HCID 21182733, compound

HRID 1387011Notes

Reaction equation

HRID 1387011 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:43]=[CH:42][C:13]([C:14]([C:16]3[C:17]4[CH:38]=[CH:37][C:36]([C:39]([NH2:41])=O)=[CH:35][C:18]=4[S:19][C:20]=3[C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)=[CH:23][CH:22]=3)=[O:15])=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>C1COCC1>[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([C:16]3[C:17]4[CH:38]=[CH:37][C:36]([C:39]#[N:41])=[CH:35][C:18]=4[S:19][C:20]=3[C:21]3[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][N:30]4[CH2:31][CH2:32][CH2:33][CH2:34]4)=[CH:25][CH:26]=3)=[O:15])=[CH:42][CH:43]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 10531590HCID 10531590, compoundHCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxide

Product 1

HCID 21182733HCID 21182733, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.1 g (5.2 mmol) of 3-[4-[2-(1-piperidinyl)ethoxy]benzoyl]-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene-6-carboxamide (Example 30, Part E) in 75 mL of anhydrous THF was added 3.1 g (13.0 mmol) of (methoxycarbonylsulfamoyl)triethylammonium hydroxide (inner salt) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred for 3 days and then filtered through a medium frit, concentrated at reduced pressure, and chromatographed on silica gel (1:1 TEA/MeOH in THF, 0 to 10%) to give 2.70 g (4.7 mmol, 90%) of a brown foam.

Workup

  1. filtrationfiltered through a medium frit
  2. concentrationconcentrated at reduced pressure
  3. customchromatographed on silica gel (1:1 TEA/MeOH in THF, 0 to 10%)

Sources & evidence

ORD record
ord-a184f75eab7d435f9b54230eba99485b
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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