Trifluoroacetic acid → HCID 28421895, compound

HRID 1403188Notes

Reaction equation

HRID 1403188 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1)#[CH:2].[CH3:10][N:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1.C(O)(C(F)(F)F)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH4+].[OH-]>O1CCOCC1>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][CH:14]2[CH2:15][CH2:16][N:11]([CH3:10])[CH2:12][CH2:13]2)[CH:6]=[CH:7][CH:8]=1)#[CH:2]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 740491-Methyl-4-piperidoneHCID 104682Benzenamine, 3-ethynyl-HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 28421895HCID 28421895, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Ethynyl-phenylamine (0.1 mL, 1 mmol) and 1-methyl-piperidin-4-one (0.15 mL, 1.2 mmol) in 1,4-dioxane (4 mL) was treated first with TFA (0.2 mL, 2.6 mmol) and then with sodium triacetoxyborohydride (318 mg, 1.5 mmol). After stirring for 2 h, 10% NH4OH was added to the reaction mixture (15 mL). Extraction with DCM (3×25 mL), drying over sodium sulfate, evaporation, purification by flash chromatography over silica gel (DCM/7N NH3 in MeOH 9/1) afforded the title compound (200 mg, 93%).

Workup

  1. extractionExtraction with DCM (3×25 mL)
  2. dry with materialdrying over sodium sulfate, evaporation, purification by flash chromatography over silica gel (DCM/7N NH3 in MeOH 9/1)

Sources & evidence

ORD record
ord-0518267162704aceaf9ad97774ff6137
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

Loading…