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Pyridine → 1-(4-(5-(5-Bromo-3-hydroxypyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanone

HRID 1809647
Notes
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Reaction equation

HRID 1809647 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](Cl)=[N:11]OS(C)(=O)=O)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].N1C=CC=CC=1.[S-:24][C:25]#[N:26].[Na+].[Br:28][C:29]1[CH:30]=[C:31]([O:36]C2C=CN=NC=2C)[C:32]([NH2:35])=[N:33][CH:34]=1>C(#N)C.O>[Br:28][C:29]1[CH:30]=[C:31]([OH:36])[C:32]([NH:35][C:25]2[S:24][N:11]=[C:10]([CH:7]3[CH2:6][CH2:5][N:4]([C:1](=[O:3])[CH3:2])[CH2:9][CH2:8]3)[N:26]=2)=[N:33][CH:34]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1049PyridineHCID 516871Sodium thiocyanateHCID 674853455-Bromo-3-(3-methylpyridazin-4-yloxy)pyridin-2-amineHCID 866410961-acetyl-N-(methylsulfonyloxy)piperidine-4-carbimidoyl chloride

Product 1

HCID 674872991-(4-(5-(5-Bromo-3-hydroxypyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanoneYield 51.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

1-Acetyl-N-(methylsulfonyloxy)piperidine-4-carbimidoyl chloride (0.15 g, 0.53 mmol), pyridine (0.13 ml, 1.6 mmol), and sodium thiocyanate (0.043 g, 0.53 mmol) were dissolved in acetonitrile (5 mL). The solution was heated to 40° C. for 40 minutes. 5-Bromo-3-(3-methylpyridazin-4-yloxy)pyridin-2-amine (0.10 g, 0.35 mmol) was added and the reaction was heated at 60° C. overnight. The solution was cooled and charged with water. The solid was filtered and dried to give 1-(4-(5-(5-bromo-3-hydroxypyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanone (0.072 g, 51%).

Workup

  1. temperaturethe reaction was heated at 60° C. overnight
  2. temperatureThe solution was cooled
  3. filtrationThe solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-f4d48ab4fd2e47f8ac1cad398ae99ab8
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08362037B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes