3-Mercaptopropanol → HCID 66113831, compound

HRID 923090Notes

Reaction equation

[Cl:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[SH:11][CH2:12][CH2:13][CH2:14][OH:15]>>[Cl:1][C:2]1[CH:9]=[C:8]([S:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

Reactant 2

HCID 882113-Mercaptopropanol

HCID 1090002-Chloro-4-fluorobenzonitrile

Product 1

HCID 66113831HCID 66113831, compound

Procedure

4 g of 2-chloro-4-fluorobenzonitrile was used in Procedure Q with 3-mercapto-1-propanol to afford 2-chloro-4-(3-hydroxypropylthio)benzonitrile. 1 g of 2-chloro-4-(3-hydroxypropylthio)benzonitrile was reacted via Procedure T to give 2-chloro-4-(3-hydroxypropylthio)benzoic acid. 1.2 g of 2-chloro-4-(3-hydroxypropylthio)benzoic acid was reacted via Procedure R to yield 2-chloro-4-(2-hydroxypropylsulfonyl)benzoic acid. 75 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 2-chloro-4-(2-hydroxypropylsulfonyl)benzoic acid via Procedure G. The product was purified on reverse phase HPLC to yield 2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(3-hydroxypropylsulfonyl)benzamide. MS (Q1) 465.0 (M)+.

Sources & evidence

ORD record: ord-57266f8b3cb7420ab9f159f61cb2f3f6
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278961B2

Reaction notes

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