Quinoxaline-2-carbaldehyde → HCID 11998277, compound

HRID 491430Notes

Reaction equation

HRID 491430 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][C:13]3[C:19]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=[CH:28][C:27]=1[CH:36]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[S:12][C:13]3[C:19]([N:20]4[CH2:25][CH2:24][N:23]([CH2:36][C:27]5[CH:28]=[N:29][C:30]6[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=6)[N:26]=5)[CH2:22][CH2:21]4)=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 594088Quinoxaline-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 57678297HCID 57678297, compound

Product 1

HCID 11998277HCID 11998277, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

The piperazine template (0.075 g, 0.213 mmol) of Example 24 was dissolved in 1,2-dichloroethane (3 mL) and treated with quinoxaline-2-carbaldehyde (0.044 g, 0.277 mmol) and glacial acetic acid (2 drops). Sodium triacetoxyborohydride (0.090 g, 0.426 mmol) was added, and the mixture was stirred at room temperature until the reaction was complete by LCMS analysis. The solvent was removed under reduced pressure, and the resulting residue was purified by RP-HPLC to yield the free base (0.0578 g, 55% yield). MS (ESI) m/z 494.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe resulting residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-e55cb59139414209ac3587dd58e64a21
Source dataset
uspto-grants-2009_05
Patent number
US07531542B2

Reaction notes

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