Sodium triacetoxyborohydride → 3-{4-[2-(4-tert-Butyl-phenyl)-imidazo[1,2-a]pyridin-5-yl]-piperazin-1-ylmethyl}-pyrido[2,3-b]pyrazine

HRID 729503Notes

Reaction equation

HRID 729503 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[N:14]3[CH:25]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N:26]1[CH:31]=[C:30]([CH:32]=O)[N:29]=[C:28]2[N:34]=[CH:35][CH:36]=[CH:37][C:27]=12.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1C(=O)CCC1.C(O)(=O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N:19]4[CH2:24][CH2:23][N:22]([CH2:32][C:30]5[N:29]=[C:28]6[N:34]=[CH:35][CH:36]=[CH:37][C:27]6=[N:26][CH:31]=5)[CH2:21][CH2:20]4)[N:14]3[CH:25]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 42605283Pyrido[2,3-b]pyrazine-3-carbaldehydeHCID 57832787HCID 57832787, compound

Product 1

HCID 156044603-{4-[2-(4-tert-Butyl-phenyl)-imidazo[1,2-a]pyridin-5-yl]-piperazin-1-ylmethyl}-pyrido[2,3-b]pyrazineYield 11%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Crude 2-(4-tert-Butyl-phenyl)-5-piperazin-1-yl-imidazo[1,2-a]pyridine (0.100 g, 0.298 mmol) and pyrido[2,3-b]pyrazine-3-carbaldehyde (0.062 g, 0.378 mmol) was dissolved in NMP (5 mL). The mixture was treated with 3 drops of glacial acetic acid, followed by sodium triacetoxyborohydride (0.126 g, 0.596 mmol.) The mixture was stirred at room temperature overnight and then purified by semipreparative RP-HPLC (Method C) followed by basification as in example 18 to obtain 0.0155 g of the title compound (11%). HPLC (Method B): r.t.=9.0 min., purity 85.2% at 210-370 nm, 81.1% at 252 nm. HRMS: calcd for C29H31N7+H+, 478.27137; found (ESI, [M+H]+), 478.271.

Workup

  1. custompurified by semipreparative RP-HPLC (Method C)

Sources & evidence

ORD record
ord-13ccc8f70e85400391b25458d616a346
Source dataset
uspto-grants-2009_09
Patent number
US07582636B2

Reaction notes

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