p-Toluenesulfonic acid monohydrate → HCID 24810096, compound

HRID 2081074Notes

Reaction equation

FC(F)(F)C(O)=O.[OH:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[C:15]2[S:23][CH:22]=[C:21]([CH2:24][O:25][C:26]3[CH:31]=[C:30]([C:32]4[O:33][C:34]([CH3:37])=[N:35][N:36]=4)[CH:29]=[CH:28][C:27]=3[CH3:38])[C:16]=2[C:17]([NH2:20])=[N:18][CH:19]=1)=[O:13].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:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[C:15]2[S:23][CH:22]=[C:21]([CH2:24][O:25][C:26]3[CH:31]=[C:30]([C:32]4[O:33][C:34]([CH3:37])=[N:35][N:36]=4)[CH:29]=[CH:28][C:27]=3[CH3:38])[C:16]=2[C:17]([NH2:20])=[N:18][CH:19]=1)=[O:13]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 4-amino-3-[2-methyl-5-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid (2-hydroxy-ethyl)-amide (0.045 g, 0.10 mmol) (from Example 14 supra) in methanol (6 mL) was treated with toluene-4-sulfonic acid hydrate (19.5 mg, 0.10 mmol) (Aldrich) and heated at 40° C. for 30 minutes. The solution was concentrated. The residue washed with diethyl ether, dissolved ino water and lyophilized to give 4-amino-3-[2-methyl-5-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid (2-hydroxy-ethyl)-amide toluene-4-sulfonic acid salt. (Yield 60.8 mg, 97%).

Workup

concentrationThe solution was concentrated
washThe residue washed with diethyl ether
dissolutiondissolved ino water

Sources & evidence

ORD record: ord-5b24e509dfd14c89b21ec8aa988e1f7e
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932390B2

Reaction notes

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