4-Chloro-3-(pyridin-2-yl)aniline → HCID 58614928, compound

HRID 922969Notes

Reaction equation

HRID 922969 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.[OH:15][CH:16]([CH3:31])[CH2:17][S:18]([CH2:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1)(=[O:20])=[O:19]>>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][C:22]([CH2:21][S:18]([CH2:17][CH:16]([OH:15])[CH3:31])(=[O:20])=[O:19])=[CH:23][CH:24]=2)=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 401519254-Chloro-3-(pyridin-2-yl)anilineHCID 66878090HCID 66878090, compound

Product 1

HCID 58614928HCID 58614928, compound

Procedure

1 g of methyl 4-(bromomethyl)benzoate was reacted with 1-mercaptopropan-2-ol via Procedure Q. 1 g of methyl 4-((2-hydroxypropylthio)methyl)benzoate was oxidized with 2 g of MCPBA in DCM at −78° C. to form crude methyl 4-((2-hydroxypropylsulfonyl)methyl)benzoate. The reaction was evaporated and purified by ISCO Combi-Flash to yield 567 mg of pure methyl 4-((2-hydroxypropylsulfonyl)methyl)benzoate which was subsequently hydrolyzed via Procedure M to give 328 mg of 4-((2-hydroxypropylsulfonyl)methyl)benzoic acid. 50 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 4-((2-hydroxypropylsulfonyl)methyl)benzoic acid via Procedure G. The crude product was purified on reverse phase HPLC to yield N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((2-hydroxypropylsulfonyl)methyl)benzamide. MS (Q1) 445.3 (M)+.

Workup

  1. customThe crude product was purified on reverse phase HPLC

Sources & evidence

ORD record
ord-6bc7337ff33d4c0dab3018da018a7cc0
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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