Hydrochloric Acid → HCID 58614766, compound

HRID 922995Notes

Reaction equation

HRID 922995 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH:32]=[CH:31][C:15]([CH2:16][N:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][C:18]3=[O:30])=[CH:14][CH:13]=2)=[O:11])=[CH:5][C:4]=1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1>>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:11])[C:12]2[CH:13]=[CH:14][C:15]([CH2:16][N:17]3[CH2:22][CH2:21][NH:20][CH2:19][C:18]3=[O:30])=[CH:31][CH:32]=2)=[CH:5][C:4]=1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 66878792HCID 66878792, compound

Product 1

HCID 58614766HCID 58614766, compound

Procedure

500 mg of methyl 4-(bromomethyl)benzoate was reacted with 480 mg of tert-butyl 3-oxopiperazine-1-carboxylate and 1 g of Cesium Carbonate in 9 mL of DMF at 45° C. Upon completion, the reaction was extracted in Ethyl Acetate 2 times saturated bicarbonate, dried over Magnesium Sulfate, filtered and concentrated to give tert-butyl 4-(4-(methoxycarbonyl)benzyl)-3-oxopiperazine-1-carboxylate. 613 mg of tert-butyl 4-(4-(methoxycarbonyl)benzyl)-3-oxopiperazine-1-carboxylate was hydrolyzed via Procedure M to give 4-((4-(tert-butoxycarbonyl)-2-oxopiperazin-1-yl)methyl)benzoic acid. 200 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 4-((4-(tert-butoxycarbonyl)-2-oxopiperazin-1-yl)methyl)benzoic acid via Procedure G. The crude product was extracted twice with saturated bicarbonate in Ethyl Acetate, dried over Magnesium Sulfate, filtered and concentrated to give crude tert-butyl 4-(4-(4-chloro-3-(pyridin-2-yl)phenylcarbamoyl)benzyl)-3-oxopiperazine-1-carboxylate. 4N HCl was subsequently added to crude tert-butyl 4-(4-(4-chloro-3-(pyridin-2-yl)phenylcarbamoyl)benzyl)-3-oxopiperazine-1-carboxylate and concentrated to give the HCl salt of N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((2-oxopiperazin-1-yl)methyl)benzamide. The reaction was purified by reverse phase HPLC to give pure N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((2-oxopiperazin-1-yl)methyl)benzamide. MS (Q1) 421.3 (M)+.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-c8a8605ce7534feebe00ed9a29db439e
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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