Piperidine → (R)-4-(3,4-dichlorobenzenesulfonyl)-3-((1-((R)-1-(4-(piperidin-1-ylmethyl)phenyl)ethyl)-1H-1,2,3-triazol-4-yl)methyl)-3.4-dihydropyrazin-2(1H)-one

HRID 1432023Notes

Reaction equation

HRID 1432023 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH:17]=[CH:16][NH:15][C:14](=[O:18])[C@H:13]2[CH2:19][C:20]2[N:21]=[N:22][N:23]([C@@H:25]([C:27]3[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=3)[CH3:26])[CH:24]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH:17]=[CH:16][NH:15][C:14](=[O:18])[C@H:13]2[CH2:19][C:20]2[N:21]=[N:22][N:23]([C@@H:25]([C:27]3[CH:34]=[CH:33][C:30]([CH2:31][N:35]4[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]4)=[CH:29][CH:28]=3)[CH3:26])[CH:24]=2)(=[O:10])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 579324524-((R)-1-(4-(((R)-1-(3 4-dichlorobenzenesulfonyl)-3-oxo-1,2,3,4-tetra-hydropyrazin-2-yl)methyl)-1H-1,2,3-triazol-1-yl)ethyl)benzaldehyde

Product 1

HCID 11621271(R)-4-(3,4-dichlorobenzenesulfonyl)-3-((1-((R)-1-(4-(piperidin-1-ylmethyl)phenyl)ethyl)-1H-1,2,3-triazol-4-yl)methyl)-3.4-dihydropyrazin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-((R)-1-(4-(((R)-1-(3,4-dichlorobenzenesulfonyl)-3-oxo-1,2,3,4-tetra-hydropyrazin-2-yl)methyl)-1H-1,2,3-triazol-1-yl)ethyl)benzaldehyde (0.150 g, 0.288 mmol) and piperidine (0.10 mL, 1.01 mmol) in 1,2-dichloroethane (10 mL) was added NaBH(OAc)3 (0.126 g, 0.594 mmol). After 18 h, the solution was diluted with 60 mL EtOAc and washed with 5% NaHCO3 (60 mL×2), brine (60 mL×2), dried over Na2SO4 and concentrated under reduced pressure. The crude product was chromatographed on SiO2 (100% CH2Cl2 to 5% 2N methanolic NH3 in CH2Cl2) to yield the title compound.

Workup

  1. washwashed with 5% NaHCO3 (60 mL×2), brine (60 mL×2)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was chromatographed on SiO2 (100% CH2Cl2 to 5% 2N methanolic NH3 in CH2Cl2)

Sources & evidence

ORD record
ord-1b5176b4cf85451ea6a4bb08c28ff139
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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