Formaldehyde → HCID 59320386, compound

HRID 655308Notes

Reaction equation

HRID 655308 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.C=O.[C:33](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:33][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

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59320197HCID 59320197, compound

Product 1

HCID 59320386HCID 59320386, compoundYield 35%

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 (194 mg, 0.4898 mmol) in dichloromethane (9 mL) was added formaldehyde (37% in water, 1.959 mmol, 147 uL). The solution was stirred at room temperature for 15 minutes and then sodium triacetoxyborohydride (260 mg, 1.22 mmol) was added. After 1 hour the solution was diluted with dichloromethane (6 mL) and washed with sodium bicarbonate (6 mL). The aqueous layer was extracted further with dichloromethane (6 mL). The combined dichloromethane layers were washed with brine (12 mL) and dried over Na2SO4. The filtrate was concentrated in vacuo onto silica gel and purified by flash chromatography (SiO2, CH2Cl2:CH3OH:NH4OH, 95:4.995:0.005-80:19.98:0.02) to return the title compound (69 mg, 35% yield). Analytical data presented in Table 2.

Workup

  1. washwashed with sodium bicarbonate (6 mL)
  2. extractionThe aqueous layer was extracted further with dichloromethane (6 mL)
  3. washThe combined dichloromethane layers were washed with brine (12 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:NH4OH, 95:4.995:0.005-80:19.98:0.02)

Sources & evidence

ORD record
ord-c14f9a67498e4aa7bbcfa5e0f81244f4
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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