Trifluoroacetic acid → HCID 58365022, compound

HRID 60310Notes

Reaction equation

HRID 60310 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[CH2:28][CH2:27][C@H:26]([NH:29]C(=O)OC(C)(C)C)[CH2:25]4)[C:6]=3[C:5]=2[CH:4]=1)#[N:2].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:29][C@H:26]1[CH2:27][CH2:28][N:24]([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)[CH2:25]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58365035(S)-tert-butyl 1-(6-cyano-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrol-4-yl)pyrrolidin-3-ylcarbamate

Product 1

HCID 58365022HCID 58365022, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 1-(6-cyano-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-4-yl)pyrrolidin-3-ylcarbamate (401 mg, 0.79 mmol) in methylene chloride (9.0 mL) was added trifluoroacetic acid (9.0 mL), and the mixture was stirred at ambient temperature for 10 minutes. The solvent was evaporated in vacuo, and the resulting residue was dissolved in methylene chloride and treated with a solution of saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo to afford the title compound as a yellow foam, which was used in the next step without any further purification (268 mg, 83%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe resulting residue was dissolved in methylene chloride
  3. additiontreated with a solution of saturated aqueous sodium bicarbonate solution
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ce98a44b267547c5b176d994fbbf4323
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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