Methanol → HCID 22462732, compound

HRID 1937168Notes

Reaction equation

HRID 1937168 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:16]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[C:20]([CH3:30])[CH:19]=3)=[C:15]([C:31]3[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH:39]4[CH2:43][NH:42][C:41](=[O:44])[N:40]4[C:45]([O:47]CC4C=CC=CC=4)=[O:46])=[CH:33][CH:32]=3)[S:14][C:13]=2[CH:55]=1)C1C=CC=CC=1.[CH3:56][OH:57].[NH4+].[OH-:59]>C(Cl)(Cl)Cl>[C:45]([OH:47])(=[O:46])[C:56]([OH:59])=[O:57].[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[C:16]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[C:20]([CH3:30])[CH:19]=3)=[C:15]([C:31]3[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH:39]4[CH2:43][NH:42][C:41](=[O:44])[NH:40]4)=[CH:33][CH:32]=3)[S:14][C:13]=2[CH:55]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 22462706HCID 22462706, compound

Product 1

HCID 22462732HCID 22462732, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

By essentially following the conditions detailed in Example 8, Part F, the free base of the title compound was prepared as a solid from 6-benzyloxy-3-[3-methyl-4-[(1-pyrrolidinyl)methyl]benzyl]-2-[4-(3-benzyloxycarbonyl-2-oxo-imidazolidin-4-ylmethoxy)phenyl]benzo[b]thiophene (Part A) in 42% yield following radial chromatography (SiO2; 1% then 3% then 5% MeOH in CHCl3 sat'd with NH4OH). The product was converted to the oxalate salt according to the conditions described in Example 1; Part G.

Sources & evidence

ORD record
ord-dda530db50a44664bdc10192d9e2bdd8
Source dataset
uspto-grants-2002_05
Patent number
US06391901B1

Reaction notes

Loading…