Methanol → HCID 22462703, compound

HRID 1937175Notes

Reaction equation

HRID 1937175 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]([NH:27]C(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@@H:46]([C:47]([OH:49])=[O:48])[NH:45][C:43](=[O:44])[CH2:42]1.[CH3:50][OH:51].[NH4+].[OH-:53]>C(Cl)(Cl)Cl>[C:47]([OH:49])(=[O:48])[C:50]([OH:53])=[O:51].[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]([NH:27][C:47]([CH:46]4[CH2:41][CH2:42][C:43](=[O:44])[NH:45]4)=[O:49])=[CH:23][CH:22]=3)=[CH:13][CH:12]=2)[CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 887MethanolHCID 7405L-Pyroglutamic AcidHCID 14923Ammonium HydroxideHCID 178478890HCID 178478890, compound

Product 1

HCID 22462703HCID 22462703, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

By essentially following the conditions described in Example 1, Part A, 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-5-carboxylic acid in 51% yield following radial chromatography (SiO2; 2% then 3% 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-3ad686b6b80545b489a06239948288e8
Source dataset
uspto-grants-2002_05
Patent number
US06391901B1

Reaction notes

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