1-Methylpiperazine → Methyl 3-{[({6-fluoro-3'-[(4-methyl-1-piperazinyl)methyl]-3-biphenylyl}methyl)(methyl)amino]carbonyl}benzoate

HRID 564529Notes

Reaction equation

HRID 564529 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]=O)[CH:9]=2)=[CH:6][C:5]([CH2:16][N:17]([CH3:30])[C:18]([C:20]2[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=2)[C:23]([O:25][CH3:26])=[O:24])=[O:19])=[CH:4][CH:3]=1.[CH3:31][N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][N:35]3[CH2:36][CH2:37][N:32]([CH3:31])[CH2:33][CH2:34]3)[CH:9]=2)=[CH:6][C:5]([CH2:16][N:17]([CH3:30])[C:18]([C:20]2[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=2)[C:23]([O:25][CH3:26])=[O:24])=[O:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 57813356Methyl 3-{[[(6-fluoro-3'-formyl-3-biphenylyl)methyl](methyl)amino]carbonyl}benzoate

Product 1

HCID 57813387Methyl 3-{[({6-fluoro-3'-[(4-methyl-1-piperazinyl)methyl]-3-biphenylyl}methyl)(methyl)amino]carbonyl}benzoateYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-{[[(6-fluoro-3′-formyl-3-biphenylyl)methyl](methyl)amino]carbonyl}benzoate (0.18 g, 0.444 mmol) in DCM (4.4 mL) was added 1-methylpiperazine (0.0542 mL, 0.488 mmol), and NaBH(OAc)3 (0.141 g, 0.666 mmol). The mixture was stirred at room temperature for 17 h and then the reaction was quenched with H2O (˜1 mL). The organic layer was separated, dried over Na2SO4 and purified by CombiFlash chromatograph to afford the title compound 0.202 g (93%). LC-MS m/z 490 (M+H)+.

Workup

  1. customthe reaction was quenched with H2O (˜1 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. custompurified by CombiFlash chromatograph

Sources & evidence

ORD record
ord-594c5f1bfb584cb1b81cb4c42589dcf1
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

Loading…