Methyl 4-(bromomethyl)benzoate → HCID 178524403, compound

HRID 633153Notes

Reaction equation

HRID 633153 reaction equation
BrCC1C=CC(C(OC)=O)=CC=1.N1N=C(S)NC=1.N1N=C(SCC2C=CC(C(OC)=O)=CC=2)NC=1.[N:36]1[N:37]=[C:38]([S:41]([CH2:43][C:44]2[CH:53]=[CH:52][C:47]([C:48]([O:50]C)=[O:49])=[CH:46][CH:45]=2)=[O:42])[NH:39][CH:40]=1.[N:54]1[N:55]=[C:56]([S:59]([CH2:62][C:63]2[CH:72]=[CH:71][C:66]([C:67]([O:69]C)=[O:68])=[CH:65][CH:64]=2)(=[O:61])=[O:60])[NH:57][CH:58]=1>>[N:36]1[N:37]=[C:38]([S:41]([CH2:43][C:44]2[CH:53]=[CH:52][C:47]([C:48]([OH:50])=[O:49])=[CH:46][CH:45]=2)=[O:42])[NH:39][CH:40]=1.[N:54]1[N:55]=[C:56]([S:59]([CH2:62][C:63]2[CH:72]=[CH:71][C:66]([C:67]([OH:69])=[O:68])=[CH:65][CH:64]=2)(=[O:61])=[O:60])[NH:57][CH:58]=1

Participants

7

Reactant 5

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 178498016HCID 178498016, compoundHCID 178498018HCID 178498018, compoundHCID 178498019HCID 178498019, compoundHCID 178527972HCID 178527972, compound

Product 2

HCID 178524403HCID 178524403, compoundHCID 178524404HCID 178524404, compound

Procedure

500 mg of methyl 4-(bromomethyl)benzoate was reacted with 4H-1,2,4-triazole-3-thiol via Procedure Q. 542 mg of methyl 4-((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-((4H-1,2,4-triazol-3-ylsulfinyl)methyl)benzoate and methyl 4-((4H-1,2,4-triazol-3-ylsulfonyl)methyl)benzoate. The mixture of 467 mg was hydrolyzed via Procedure M to give 4-((4H-1,2,4-triazol-3-ylsulfinyl)methyl)benzoic acid and 4-((4H-1,2,4-triazol-3-ylsulfonyl)methyl)benzoic acid. 107 mg of the mixture of 4-((4H-1,2,4-triazol-3-ylsulfinyl)methyl)benzoic acid and 4-((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 4-((4H-1,2,4-triazol-3-ylsulfinyl)methyl)-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide. MS (Q1) 438.1 (M)+.

Workup

  1. customto give
  2. additionThe mixture of 467 mg

Sources & evidence

ORD record
ord-64b667ef917d44afb933aa4ea802f400
Source dataset
uspto-grants-2016_04
Patent number
US09321761B2

Reaction notes

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