1-(3-Bromopropyl)pyrrolidine hydrobromide → N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]-3-{[4-(3-pyrrolidin-1-ylpropoxy)phenyl]thio}pyridine-2-carboxamide

HRID 2196609Notes

Reaction equation

HRID 2196609 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:10]([C:22]([NH:24][C:25]3[S:29][N:28]=[C:27]([CH3:30])[N:26]=3)=[O:23])=[N:11][C:12]([S:15][C:16]3[N:20]([CH3:21])[CH:19]=[N:18][N:17]=3)=[CH:13][CH:14]=2)=[CH:4][CH:3]=1.Br.Br[CH2:33][CH2:34][CH2:35][N:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1>>[CH3:30][C:27]1[N:26]=[C:25]([NH:24][C:22]([C:10]2[C:9]([S:8][C:5]3[CH:4]=[CH:3][C:2]([O:1][CH2:33][CH2:34][CH2:35][N:36]4[CH2:40][CH2:39][CH2:38][CH2:37]4)=[CH:7][CH:6]=3)=[CH:14][CH:13]=[C:12]([S:15][C:16]3[N:20]([CH3:21])[CH:19]=[N:18][N:17]=3)[N:11]=2)=[O:23])[S:29][N:28]=1

Participants

3

Reactant 2

HCID 201359201-(3-Bromopropyl)pyrrolidine hydrobromideHCID 597062523-[(4-hydroxyphenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]pyridine-2-carboxamide

Product 1

HCID 25066400N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]-3-{[4-(3-pyrrolidin-1-ylpropoxy)phenyl]thio}pyridine-2-carboxamideYield 16.9%

Procedure

Using 19 mg of 3-[(4-hydroxyphenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]pyridine-2-carboxamide obtained in Reference Example (step 3) and 13 mg of 1-(3-bromopropyl)pyrrolidine hydrobromide obtained in the step 1, 4 mg of the entitled compound was obtained as a pale yellow solid in the same method as in Example 2 or in accordance with the method or by combining it with an ordinary method.

Workup

  1. customobtained in the step 1

Sources & evidence

ORD record
ord-cc87139ad82f446b95ccc30fbfc27d3c
Source dataset
uspto-grants-2012_12
Patent number
US08338460B2

Reaction notes

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