Hydrochloric Acid → HCID 178478889, compound

HRID 1937173Notes

Reaction equation

HRID 1937173 reaction equation
[ClH:1].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.[NH:41]1[CH:45]=CC(C(O)=O)=N1.[NH4+].[OH-].Cl>C(Cl)(Cl)Cl.CO>[ClH:1].[ClH:1].[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:22]=[CH:23][C:24]([NH:27][C:28]([C:30]4[CH:34]=[CH:45][NH:41][N:31]=4)=[O:29])=[CH:25][CH:26]=3)=[CH:39][CH:40]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 178478890HCID 178478890, compoundHCID 178524567HCID 178524567, compound

Product 1

HCID 178478889HCID 178478889, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

By essentially following the conditions described in Example 16, Part E, the free base of the title compound was prepared as a solid from 2-(4-aminophenyl)-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene (Example 16; Part D) and 3-pyrazole carboxylic acid in 48% yield following radial chromatography (SiO2; 1% then 3% then 5% MeOH in CHCl3 sat'd with NH4OH). The solid was taken up in 5 mL MeOH, and the solution was treated with 1 mL of 1 N HCl. The solution was concentrated to give the title compound.

Workup

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

Sources & evidence

ORD record
ord-c49c0b2a68484b918f97104a854be811
Source dataset
uspto-grants-2002_05
Patent number
US06391901B1

Reaction notes

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