Trifluoroacetic acid → 4-(piperazin-1-yl)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 60265Notes

Reaction equation

HRID 60265 reaction equation
[C:1]([C:3]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:7]3[N:20]=[CH:21][CH:22]=[C:23]([N:24]4[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]4)[C:6]=3[C:5]=2[CH:4]=1)#[N:2].FC(F)(F)C(O)=O>C(Cl)Cl>[N:24]1([C:23]2[C:6]3[C:5]4[CH:4]=[C:3]([C:1]#[N:2])[N:11]=[CH:10][C:9]=4[N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:7]=3[N:20]=[CH:21][CH:22]=2)[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58365108HCID 58365108, compound

Product 1

HCID 672574164-(piperazin-1-yl)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-butyl 4-(6-cyano-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-4-yl)piperazine-1-carboxylate (440 mg, 0.8 mmol) in methylene chloride (3 mL) was treated with trifluoroacetic acid (0.6 mL, 8.0 mmol) and the reaction mixture was stirred at ambient temperature for 4 hours. The reaction mixture was diluted with methylene chloride (50 mL) and washed with saturated aqueous sodium carbonate solution (10 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified flash chromatography (silica, 4 g, ISCO, 0-10% methylene chloride in methanol) to afford the title compound as a white foam, which was used in the next step without any further purification (200 mg, 60%).

Workup

  1. washwashed with saturated aqueous sodium carbonate solution (10 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified flash chromatography (silica, 4 g, ISCO, 0-10% methylene chloride in methanol)

Sources & evidence

ORD record
ord-bb123d954ae5472395a5ab959220009d
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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