Trifluoroacetic acid → HCID 22462762, compound

HRID 1937174Notes

Reaction equation

HRID 1937174 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]4N=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.C(C1C[CH2:47][C:46](=[O:49])[CH2:45]1)(O)=O.[NH4+].[OH-].[C:52]([C:56]([OH:58])=[O:57])([F:55])([F:54])[F:53]>C(Cl)(Cl)Cl.CO>[F:53][C:52]([F:55])([F:54])[C:56]([OH:58])=[O:57].[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:22]=[CH:23][C:24]([NH:27][C:28]([CH:30]4[CH2:34][CH2:47][C:46](=[O:49])[CH2:45]4)=[O:29])=[CH:25][CH:26]=3)=[CH:13][CH:12]=2)[CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 2277983-Oxocyclopentanecarboxylic acidHCID 178478890HCID 178478890, compound

Product 1

HCID 22462762HCID 22462762, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×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 3-carboxycyclopentanone in 98% yield following radial chromatography (SiO2; 1% then 2% then 5% MeOH in CHCl3 sat'd with NH4OH). The solid was taken up in 5 mL of MeOH and was treated with 1.2 eq of CF3CO2H. The solution was concentrated in vacuo to give the title compound.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customto give the title compound

Sources & evidence

ORD record
ord-5b6089006ea644bdb5965417cb1cf09f
Source dataset
uspto-grants-2002_05
Patent number
US06391901B1

Reaction notes

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