Hydrochloric Acid → N-(3-chloro-4-(4-chloro-3-(pyridin-2-yl)phenylcarbamoyl)benzyl)picolinamide

HRID 922952Notes

Reaction equation

HRID 922952 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[C:17](=[O:32])[NH:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH:20]=1)[CH2:5][NH:6][C:7](=[O:13])OC(C)(C)C.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[C:17](=[O:32])[NH:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH:20]=1)[CH2:5][NH:6][C:7](=[O:13])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1.[NH2:6][CH2:5][C:4]1[CH:14]=[CH:15][C:16]([C:17]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[CH:20]=2)=[O:32])=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66877970Tert-butyl 3-chloro-4-(4-chloro-3-(pyridin-2-yl)phenylcarbamoyl)benzylcarbamate

Product 2

HCID 58614823N-(3-chloro-4-(4-chloro-3-(pyridin-2-yl)phenylcarbamoyl)benzyl)picolinamideHCID 668770292-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(aminomethyl)benzamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

75 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 4-((tert-butoxycarbonylamino)methyl)-2-chlorobenzoic acid via Procedure G to yield tert-butyl 3-chloro-4-(4-chloro-3-(pyridin-2-yl)phenylcarbamoyl)benzylcarbamate. Tert-butyl 3-chloro-4-(4-chloro-3-(pyridin-2-yl)phenylcarbamoyl)benzylcarbamate was subsequently treated with 4N HCl in Dioxane to remove the Boc protecting group and form the HCl salt of 4-(aminomethyl)-2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide. 54 mg of the crude HCl salt of 4-(aminomethyl)-2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide was coupled to picolinic acid via Procedure G. The crude product was purified by reverse phase HPLC to yield N-(3-chloro-4-(4-chloro-3-(pyridin-2-yl)phenylcarbamoyl)benzyl)picolinamide. MS (Q1) 477.3 (M)+.

Workup

  1. customto remove the Boc protecting group

Sources & evidence

ORD record
ord-ba3b763ab39b4a89913c799e0aee3808
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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