Hydrochloric Acid → HCID 66994445, compound

HRID 1806157Notes

Reaction equation

HRID 1806157 reaction equation
[F:1][C:2]1[CH:44]=[CH:43][C:5]([O:6][C:7]2[C:8]([NH:23][C:24]3[S:28][N:27]=[C:26]([CH2:29][CH:30]4[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]4)[N:25]=3)=[N:9][CH:10]=[C:11]([S:13][C:14]3[CH:19]=[CH:18][N:17]=[C:16]4[CH:20]=[CH:21][S:22][C:15]=34)[CH:12]=2)=[CH:4][CH:3]=1.CO.C(Cl)[Cl:48].[ClH:50]>O1CCOCC1>[ClH:48].[ClH:50].[ClH:48].[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[C:8]([NH:23][C:24]3[S:28][N:27]=[C:26]([CH2:29][CH:30]4[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]4)[N:25]=3)=[N:9][CH:10]=[C:11]([S:13][C:14]3[CH:19]=[CH:18][N:17]=[C:16]4[CH:20]=[CH:21][S:22][C:15]=34)[CH:12]=2)=[CH:43][CH:44]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6344DichloromethaneHCID 66995216HCID 66995216, compound

Product 1

HCID 66994445HCID 66994445, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 10 mL round-bottomed flask was charged with tert-butyl 4-((5-(3-(4-fluorophenoxy)-5-(thieno[3,2-b]pyridin-7-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)methyl)piperidine-1-carboxylate (52.2 mg, 0.0802 mmol) and a 1:1 mix of methanol and CH2Cl2 (4 mL). 4N HCl in dioxane (2 mL) was added and the reaction stirred at room temperature for 10 minutes. The solvent was removed to afford crude 3-(4-fluorophenoxy)-N-(3-(piperidin-4-ylmethyl)-1,2,4-thiadiazol-5-yl)-5-(thieno[3,2-b]pyridin-7-ylthio)pyridin-2-amine trihydrochloride (52.9 mg, 100%).

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-8ce671a7a8e041998ab3243b816fe915
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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