Acetaldehyde → HCID 73294554, compound

HRID 1398048Notes

Reaction equation

HRID 1398048 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[NH2:15])[N:11]=[C:10]([CH:20]3[CH2:25][C:24]([CH3:27])([CH3:26])[O:23][C:22]([CH3:29])([CH3:28])[CH2:21]3)[CH:9]=2)=[CH:4][CH:3]=1.[CH:30](=O)[CH3:31].C([BH3-])#N.[Na+].C([O-])(O)=O.[Na+]>C1COCC1.O.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[NH:15][CH2:30][CH3:31])[N:11]=[C:10]([CH:20]3[CH2:25][C:24]([CH3:27])([CH3:26])[O:23][C:22]([CH3:29])([CH3:28])[CH2:21]3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 177AcetaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 73292040HCID 73292040, compound

Product 1

HCID 73294554HCID 73294554, compoundYield 53.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(5-(4-chlorophenyl)-3-(2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)-1H-pyrazol-1-yl)aniline (Example 62) (50 mg, 0.12 mmol, 1 eq) in THF (2 mL) was added acetaldehyde (0.028 mL, 0.49 mmol, 4 eq). After 15 min, sodium cyanoborohydride (61 mg, 0.98 mmol, 8 eq) and acetic acid (0.1 mL) were added and the solution stirred 3 days. Water and NaHCO3 were added, extracted with DCM, dried over MgSO4 and concentrated. Purification by column chromatography (8 g) eluting with 15 to 30% EtOAc/hex gave the title compound (28.3 mg, 50%).

Workup

  1. extractionextracted with DCM
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customPurification by column chromatography (8 g)
  5. washeluting with 15 to 30% EtOAc/hex

Sources & evidence

ORD record
ord-70c3da6b3dfc44a4ae15490fd9bbc612
Source dataset
uspto-grants-2014_12
Patent number
US08901314B2

Reaction notes

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