4-Chloro-3-(pyridin-2-yl)aniline → HCID 178522072, compound

HRID 923003Notes

Reaction equation

[N:1]1[N:2]=[C:3]([S:6]([CH2:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)=[O:7])[NH:4][CH:5]=1.N1N=C(S(CC2C=CC(C(O)=O)=CC=2)(=O)=O)NC=1.[Cl:36][C:37]1[CH:43]=[CH:42][C:40]([NH2:41])=[CH:39][C:38]=1[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=1>>[N:1]1[N:2]=[C:3]([S:6]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([NH:41][C:40]3[CH:42]=[CH:43][C:37]([Cl:36])=[C:38]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=4)[CH:39]=3)=[O:15])=[CH:16][CH:17]=2)=[O:7])[NH:4][CH:5]=1

Participants

Reactant 3

HCID 401519254-Chloro-3-(pyridin-2-yl)aniline

HCID 178524403HCID 178524403, compound

HCID 178524404HCID 178524404, compound

Product 1

HCID 178522072HCID 178522072, 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

customThe mixture was separated on reverse phase HPLC

Sources & evidence

ORD record: ord-84bddb70df3f4d18a6170d7b69d6549e
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278961B2

Reaction notes

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