Acetaldehyde → HCID 59320202, compound

HRID 655299Notes

Reaction equation

HRID 655299 reaction equation
[NH:1]1[CH2:4][CH:3]([N:5]2[CH:9]=[C:8]([C:10]3[CH:11]=[N:12][C:13]4[C:18]([CH:19]=3)=[CH:17][C:16]([CH2:20][C:21]3[N:25]5[N:26]=[C:27]([CH3:30])[CH:28]=[CH:29][C:24]5=[N:23][N:22]=3)=[CH:15][CH:14]=4)[CH:7]=[N:6]2)[CH2:2]1.[CH:31](=O)[CH3:32].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:31]([N:1]1[CH2:4][CH:3]([N:5]2[CH:9]=[C:8]([C:10]3[CH:11]=[N:12][C:13]4[C:18]([CH:19]=3)=[CH:17][C:16]([CH2:20][C:21]3[N:25]5[N:26]=[C:27]([CH3:30])[CH:28]=[CH:29][C:24]5=[N:23][N:22]=3)=[CH:15][CH:14]=4)[CH:7]=[N:6]2)[CH2:2]1)[CH3:32]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59320197HCID 59320197, compound

Product 1

HCID 59320202HCID 59320202, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 3-(1-azetidin-3-yl-1H-pyrazol-4-yl)-6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinoline (50 mg, 0.126 mmol) in dichloromethane (3 mL) was added acetaldehyde (15 uL, 0.505 mmol). The solution was stirred at room temperature for 15 minutes and then sodium triacetoxyborohydride (67 mg, 0.136) was added. After 1 hour the solution was diluted with dichloromethane (1.5 mL) and washed with sodium bicarbonate (1.5 mL). The aqueous layer was extracted further with dichloromethane (1.5 mL). The combined dichloromethane layers were washed with brine (3 mL) and dried over Na2SO4. The filtrate was concentrated in vacuo onto silica gel and purified by flash chromatography (SiO2, CH2Cl2:CH3OH 100:0-90:10) to return the title compound (4.8 mg, 9% yield). Analytical data presented in Table 2.

Workup

  1. washwashed with sodium bicarbonate (1.5 mL)
  2. extractionThe aqueous layer was extracted further with dichloromethane (1.5 mL)
  3. washThe combined dichloromethane layers were washed with brine (3 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationThe filtrate was concentrated in vacuo onto silica gel
  6. custompurified by flash chromatography (SiO2, CH2Cl2:CH3OH 100:0-90:10)

Sources & evidence

ORD record
ord-b80831ca34db4a418eb90be6c4c6caf4
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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