Methanol → HCID 22462698, compound

HRID 1937178Notes

Reaction equation

HRID 1937178 reaction equation
Cl.Cl.[N:3]1([CH2:8][CH2:9][O:10][C:11]2[CH:40]=[CH:39][C:14]([CH2:15][C:16]3[C:17]4[CH:38]=[CH:37][CH:36]=[CH:35][C:18]=4[S:19][C:20]=3[C:21]3[CH:26]=[CH:25][C:24](NC(C4N=CNC=4)=O)=[CH:23][CH:22]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1.[CH2:41]1[C:45](=[O:46])[NH:44][CH2:43][CH:42]1[CH2:47][C:48]([OH:50])=[O:49].[CH3:51][OH:52].[NH4+].[OH-:54]>C(Cl)(Cl)Cl>[C:48]([OH:50])(=[O:49])[C:51]([OH:54])=[O:52].[N:3]1([CH2:8][CH2:9][O:10][C:11]2[CH:40]=[CH:39][C:14]([CH2:15][C:16]3[C:17]4[CH:38]=[CH:37][CH:36]=[CH:35][C:18]=4[S:19][C:20]=3[C:21]3[CH:26]=[CH:25][C:24]([C:48](=[O:49])[CH2:47][CH:42]4[CH2:41][C:45](=[O:46])[NH:44][CH2:43]4)=[CH:23][CH:22]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 215735475-oxo-3-Pyrrolidineacetic acidHCID 178478890HCID 178478890, compound

Product 1

HCID 22462698HCID 22462698, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

By essentially following the conditions described in Example 1, Part F, the free base of the title compound was prepared as a foam from 2-(4-aminophenyl)-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene (Example 16; Part D) and 2-pyrrolidinone-4-acetic acid in 67% yield following radial chromatography (SiO2; 1% then 2% then 4% MeOH in CHCl3 sat'd with NH4OH). The product was converted to the oxalate salt according to the proceedure described in Example 1, Part G.

Sources & evidence

ORD record
ord-4b056384e5ed40bf9c7636def69963a2
Source dataset
uspto-grants-2002_05
Patent number
US06391901B1

Reaction notes

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