p-Toluenesulfonic acid monohydrate → 4-Amino-3-{5-[1-(4-chloro-benzyl)-1h-[1,2,3]triazol-4-yl]-2-methyl-phenoxymethyl}-thieno[3,2-c]pyridine-7-carboxylic acid (2-hydroxy-ethyl)-amide toluene-4-sulfonic acid salt

HRID 2081096Notes

Reaction equation

HRID 2081096 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[C:8]2[S:16][CH:15]=[C:14]([CH2:17][O:18][C:19]3[CH:24]=[C:23]([C:25]4[N:26]=[N:27][N:28]([CH2:30][C:31]5[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=5)[CH:29]=4)[CH:22]=[CH:21][C:20]=3[CH3:38])[C:9]=2[C:10]([NH2:13])=[N:11][CH:12]=1)=[O:6].O.[C:40]1([CH3:50])[CH:45]=[CH:44][C:43]([S:46]([OH:49])(=[O:48])=[O:47])=[CH:42][CH:41]=1>CO>[C:40]1([CH3:50])[CH:41]=[CH:42][C:43]([S:46]([OH:49])(=[O:47])=[O:48])=[CH:44][CH:45]=1.[OH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[C:8]2[S:16][CH:15]=[C:14]([CH2:17][O:18][C:19]3[CH:24]=[C:23]([C:25]4[N:26]=[N:27][N:28]([CH2:30][C:31]5[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=5)[CH:29]=4)[CH:22]=[CH:21][C:20]=3[CH3:38])[C:9]=2[C:10]([NH2:13])=[N:11][CH:12]=1)=[O:6]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 24810239HCID 24810239, compound

Product 1

HCID 248102404-Amino-3-{5-[1-(4-chloro-benzyl)-1h-[1,2,3]triazol-4-yl]-2-methyl-phenoxymethyl}-thieno[3,2-c]pyridine-7-carboxylic acid (2-hydroxy-ethyl)-amide toluene-4-sulfonic acid salt

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To solution of 4-amino-3-{5-[1-(4-chloro-benzyl)-1H-[1,2,3]triazol-4-yl]-2-methyl-phenoxymethyl}-thieno[3,2-c]pyridine-7-carboxylic acid (2-hydroxy-ethyl)-amide (0.159 g, 0.29 mmol) (from Example 37 supra) in methanol (10 mL) was treated with toluene-4-sulfonic acid hydrate (61.0 mg, 0.319 mmol) and heated at room temperature for 40 minutes. The solution was concentrated. The residue washed with diethyl ether, dissolved in water and lyophilized to 4-amino-3-{5-[1-(4-chloro-benzyl)-1H-[1,2,3]triazol-4-yl]-2-methyl-phenoxymethyl}-thieno[3,2-c]pyridine-7-carboxylic acid (2-hydroxy-ethyl)-amide 1.5 toluene-4-sulfonic acid salt. (Yield 0.21 g, 100%).

Workup

  1. concentrationThe solution was concentrated
  2. washThe residue washed with diethyl ether
  3. dissolutiondissolved in water

Sources & evidence

ORD record
ord-bf7c645fb7fd4a84baa4983e314a66c4
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

Loading…