Acetic Acid → HCID 10431406, compound

HRID 1437304Notes

Reaction equation

HRID 1437304 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][C:11]([C:20]([N:22]3[CH2:27][CH:26]([CH3:28])[NH:25][CH:24]([CH3:29])[CH2:23]3)=[O:21])=[N:10]2)=[CH:5][CH:4]=1.C=O.[C:32](O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:12][C:11]([C:20]([N:22]3[CH2:27][CH:26]([CH3:28])[N:25]([CH3:32])[CH:24]([CH3:29])[CH2:23]3)=[O:21])=[N:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 10045985HCID 10045985, compound

Product 1

HCID 10431406HCID 10431406, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-[1-(6-Methoxy-3-pyridyl)-5-phenylpyrazole-3-carbonyl]-2,6-dimethylpiperazine (29.7 mg) obtained in Example 22 was dissolved in ethanol (2.0 mL). To the solution, 35% aqueous formalin solution (0.0325 mL), acetic acid (0.0217 mL), and sodium cyanoborohydride (9.2 mg) were added at room temperature, followed by stirring for 1.5 hours. The reaction mixture was partitioned between aqueous sodium hydrogencarbonate and chloroform at 0° C. The aqueous layer was further extracted with chloroform. The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate anhydrate. After filtration, the solvent was removed under reduced pressure, and the residue was brought to dryness, to thereby give the title compound (40 mg, quantitative amount).

Workup

  1. customThe reaction mixture was partitioned between aqueous sodium hydrogencarbonate and chloroform at 0° C
  2. extractionThe aqueous layer was further extracted with chloroform
  3. washwashed with saturated brine
  4. dry with materialby drying over sodium sulfate anhydrate
  5. filtrationAfter filtration
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ed30a31f729e4ca595d93c439f09d2a5
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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