Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:25]=[CH:24][C:14]([CH2:15][NH:16][C:17](=O)[O:18]C(C)(C)C)=[CH:13][CH:12]=2)=[O:10])=[CH:4][C:3]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([CH2:15][NH:16][C:17](=[O:18])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)=[CH:24][CH:25]=2)=[O:10])=[CH:4][C:3]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1.[NH2:16][CH2:15][C:14]1[CH:13]=[CH:12][C:11]([C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[CH:4]=2)=[O:10])=[CH:25][CH:24]=1Participants
5
Reactant 2
Product 2
Reagents, catalysts & solvents 1
Procedure
75 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 4-((tert-butoxycarbonylamino)methyl)benzoic acid via Procedure G to yield tert-butyl 4-(4-chloro-3-(pyridin-2-yl)phenylcarbamoyl)benzylcarbamate. Tert-butyl 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)-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide. 50 mg of the crude HCl salt of 4-(aminomethyl)-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-(4-(4-chloro-3-(pyridin-2-yl)phenylcarbamoyl)benzyl)picolinamide. MS (Q1) 443.3 (M)+.
Workup
- customto remove the Boc protecting group
Sources & evidence
- ORD record
- ord-9d4488c169b946bba6db5cb84a914b4e
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07888364B2
Linked notes
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