Pyridine → Tert-butyl 4-(5-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidine-1-carboxylate

HRID 1809651Notes

Reaction equation

HRID 1809651 reaction equation
Cl[C:2](=[N:16]OS(C)(=O)=O)[CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[S-:22][C:23]#[N:24].[Na+].N1C=CC=CC=1.[CH3:32][C:33]1[C:38]([O:39][C:40]2[C:41]([NH2:53])=[N:42][CH:43]=[C:44]([S:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=3)[CH:45]=2)=[CH:37][CH:36]=[CH:35][N:34]=1>>[CH3:32][C:33]1[C:38]([O:39][C:40]2[C:41]([NH:53][C:23]3[S:22][N:16]=[C:2]([CH:3]4[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:7][CH2:8]4)[N:24]=3)=[N:42][CH:43]=[C:44]([S:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=3)[CH:45]=2)=[CH:37][CH:36]=[CH:35][N:34]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 516871Sodium thiocyanateHCID 674857913-(2-Methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-amineHCID 86640985Tert-butyl 4-(chloro(methylsulfonyloxyimino)methyl)piperidine-1-carboxylate

Product 1

HCID 68708604Tert-butyl 4-(5-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidine-1-carboxylateYield 85.3%

Procedure

Following the procedure in Example 51, Step G and using tert-butyl 4-(chloro(methylsulfonyloxyimino)methyl)piperidine-1-carboxylate (34.3 g, 101 mmol), sodium thiocyanate (9.40 g, 116 mmol), pyridine (28.1 ml, 348 mmol), and 3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-amine (24.0 g, 77.3 mmol) provided tert-butyl 4-(5-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidine-1-carboxylate (38.1 g, 65.9 mmol, 85.3% yield).

Sources & evidence

ORD record
ord-a739d80ad8c743a393af6876656deae5
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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