Acetaldehyde → HCID 58365198, compound

HRID 60290Notes

Reaction equation

HRID 60290 reaction equation
[CH3:1][C:2]1([CH2:8][O:9][C:10]2[C:18]3[C:17]4[CH:19]=[C:20]([C:23]#[N:24])[N:21]=[CH:22][C:16]=4[N:15]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:14]=3[N:13]=[CH:12][CH:11]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH:33](=O)[CH3:34].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH2:33]([N:5]1[CH2:4][CH2:3][C:2]([CH2:8][O:9][C:10]2[C:18]3[C:17]4[CH:19]=[C:20]([C:23]#[N:24])[N:21]=[CH:22][C:16]=4[N:15]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:31])([CH3:30])[CH3:32])[C:14]=3[N:13]=[CH:12][CH:11]=2)([CH3:1])[CH2:7][CH2:6]1)[CH3:34]

Participants

6

Reactant 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67247661HCID 67247661, compound

Product 1

HCID 58365198HCID 58365198, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 4-((4-methylpiperidin-4-yl)methoxy)-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (75 mg, 0.17 mmol) in methylene chloride (1.1 mL) was added acetaldehyde (14 uL, 0.25 mmol) and sodium triacetoxyborohydride (53 mg, 0.25 mmol), and the mixture was stirred at ambient temperature for 10 minutes. The reaction mixture was diluted with saturated aqueous sodium bicarbonate solution (50 mL) and methylene chloride (50 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified flash chromatography (silica, 4 g, ISCO, 0-20% methanol in methylene chloride) to afford the title compound as a yellow solid, which was used in the next step without any further purification (58 mg, 73%).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. custompurified flash chromatography (silica, 4 g, ISCO, 0-20% methanol in methylene chloride)

Sources & evidence

ORD record
ord-4a5916f0916b4e7b993371951b178d59
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

Loading…