Methyl 4-(bromomethyl)benzoate → 4-((4-methyl-4H-1,2,4-triazol-3-ylsulfinyl)methyl)benzoic acid

HRID 633156Notes

Reaction equation

HRID 633156 reaction equation
BrCC1C=CC(C(OC)=O)=CC=1.CN1C=NN=C1S.CN1C=NN=C1SCC1C=CC(C(OC)=O)=CC=1.[CH3:38][N:39]1[CH:43]=[N:42][N:41]=[C:40]1[S:44]([CH2:46][C:47]1[CH:56]=[CH:55][C:50]([C:51]([O:53]C)=[O:52])=[CH:49][CH:48]=1)=[O:45].[CH3:57][N:58]1[CH:62]=[N:61][N:60]=[C:59]1[S:63]([CH2:66][C:67]1[CH:76]=[CH:75][C:70]([C:71]([O:73]C)=[O:72])=[CH:69][CH:68]=1)(=[O:65])=[O:64]>>[CH3:38][N:39]1[CH:43]=[N:42][N:41]=[C:40]1[S:44]([CH2:46][C:47]1[CH:56]=[CH:55][C:50]([C:51]([OH:53])=[O:52])=[CH:49][CH:48]=1)=[O:45].[CH3:57][N:58]1[CH:62]=[N:61][N:60]=[C:59]1[S:63]([CH2:66][C:67]1[CH:76]=[CH:75][C:70]([C:71]([OH:73])=[O:72])=[CH:69][CH:68]=1)(=[O:64])=[O:65]

Participants

7

Reactant 5

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 728234methyl 4-{[(4-methyl-4H-1,2,4-triazol-3-yl)sulfanyl]methyl}benzoateHCID 66896432methyl 4-((4-methyl-4H-1,2,4-triazol-3-ylsulfonyl)methyl)benzoateHCID 66896739methyl 4-((4-methyl-4H-1,2,4-triazol-3-ylsulfinyl)methyl)benzoateHCID 178481306HCID 178481306, compound

Product 2

HCID 668955914-((4-methyl-4H-1,2,4-triazol-3-ylsulfinyl)methyl)benzoic acidHCID 668961684-((4-methyl-4H-1,2,4-triazol-3-ylsulfonyl)methyl)benzoic acid

Procedure

500 mg of methyl 4-(bromomethyl)benzoate was reacted with 4-methyl-4H-1,2,4-triazole-3-thiol via Procedure Q. 804 mg of methyl 4-((4-methyl-4H-1,2,4-triazol-3-ylthio)methyl)benzoate was subsequently reacted via Procedure R to give an approximate 1:9 mixture of methyl 4-((4-methyl-4H-1,2,4-triazol-3-ylsulfinyl)methyl)benzoate and methyl 4-((4-methyl-4H-1,2,4-triazol-3-ylsulfonyl)methyl)benzoate. The mixture of 740 mg was hydrolyzed via Procedure M to give 4-((4-methyl-4H-1,2,4-triazol-3-ylsulfinyl)methyl)benzoic acid and 4-((4-methyl-4H-1,2,4-triazol-3-ylsulfonyl)methyl)benzoic acid. 114 mg of the mixture of 4-((4-methyl-4H-1,2,4-triazol-3-ylsulfinyl)methyl)benzoic acid and 4-((4-methyl-4H-1,2,4-triazol-3-ylsulfonyl)methyl)benzoic acid was coupled to 75 mg of 4-chloro-3-(pyridin-2-yl)aniline via Procedure G. The mixture was separated on reverse phase HPLC to give N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((4-methyl-4H-1,2,4-triazol-3-ylsulfinyl)methyl)benzamide. MS (Q1) 452.3 (M)+.

Workup

  1. customto give
  2. additionThe mixture of 740 mg

Sources & evidence

ORD record
ord-e3f6db2089174138815a78c11a14df7c
Source dataset
uspto-grants-2016_04
Patent number
US09321761B2

Reaction notes

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