Hydrochloric Acid → HCID 66994445, compound

HRID 335231Notes

Reaction equation

HRID 335231 reaction equation
[ClH:1].Cl.Cl.S1C2C(=NC=CC=2)C=C1N.[F:14][C:15]1[CH:57]=[CH:56][C:18]([O:19][C:20]2[C:21]([NH:36][C:37]3[S:41][N:40]=[C:39]([CH2:42][CH:43]4[CH2:48][CH2:47][N:46](C(OC(C)(C)C)=O)[CH2:45][CH2:44]4)[N:38]=3)=[N:22][CH:23]=[C:24]([S:26][C:27]3[CH:32]=[CH:31][N:30]=[C:29]4[CH:33]=[CH:34][S:35][C:28]=34)[CH:25]=2)=[CH:17][CH:16]=1.CO.Cl>O1CCOCC1.C(Cl)Cl>[ClH:1].[ClH:1].[ClH:1].[F:14][C:15]1[CH:16]=[CH:17][C:18]([O:19][C:20]2[C:21]([NH:36][C:37]3[S:41][N:40]=[C:39]([CH2:42][CH:43]4[CH2:44][CH2:45][NH:46][CH2:47][CH2:48]4)[N:38]=3)=[N:22][CH:23]=[C:24]([S:26][C:27]3[CH:32]=[CH:31][N:30]=[C:29]4[CH:33]=[CH:34][S:35][C:28]=34)[CH:25]=2)=[CH:56][CH:57]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 66995216HCID 66995216, compoundHCID 86678232HCID 86678232, compound

Product 1

HCID 66994445HCID 66994445, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Preparation of 3-(4-fluorophenoxy)-N-(3-(piperidin-4-ylmethyl)-1,2,4-thiadiazol-5-yl)-5-(thieno[3,2-b]pyridin-2-amine trihydrochloride: 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-f82b866f410041fda57ac3c015de2d87
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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