Methanol → HCID 22462675, compound

HRID 1937179Notes

Reaction equation

HRID 1937179 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:28]([C:30]4[N:31]=CN[CH:34]=4)=[O:29])=[CH:23][CH:22]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1.[O:41]1[C:45]([C:46]([OH:48])=[O:47])=CC=N1.CO.[NH4+].[OH-]>C(Cl)(Cl)Cl>[C:46]([OH:48])(=[O:47])[C:45]([OH:10])=[O:41].[N:3]1([CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][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:28]([C:30]4[CH:34]=[CH:45][O:41][N:31]=4)=[O:29])=[CH:23][CH:22]=3)=[CH:39][CH:40]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 20605991,2-Oxazole-5-carboxylic acidHCID 178478890HCID 178478890, compound

Product 1

HCID 22462675HCID 22462675, compoundYield 95%

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 5-isoxazolecarboxylic acid in 95% yield following radial chromatography (SiO2; 1% then 2% then 3% 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-1ce897789f7e4a0eb1ccaa20c26c0820
Source dataset
uspto-grants-2002_05
Patent number
US06391901B1

Reaction notes

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