Trifluoroacetic acid → HCID 58438546, compound

HRID 1898625Notes

Reaction equation

HRID 1898625 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([C@H:11]([NH:16][C:17]([C:19]2[C:27]3[C:22](=[N:23][CH:24]=[C:25]([C:28]4[N:29]=[CH:30][N:31]([CH2:33][CH:34]5[CH2:36][CH2:35]5)[CH:32]=4)[N:26]=3)[N:21](COCC[Si](C)(C)C)[CH:20]=2)=[O:18])[C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2].FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]([CH:3]1[CH2:4][CH2:5][N:6]([C:9]([C@H:11]([NH:16][C:17]([C:19]2[C:27]3[C:22](=[N:23][CH:24]=[C:25]([C:28]4[N:29]=[CH:30][N:31]([CH2:33][CH:34]5[CH2:35][CH2:36]5)[CH:32]=4)[N:26]=3)[NH:21][CH:20]=2)=[O:18])[C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][CH2:8]1)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67385987HCID 67385987, compound

Product 1

HCID 58438546HCID 58438546, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(1-cyclopropylmethyl-1H-imidazol-4-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(4-cyano-piperidine-1-carbonyl)-2,2-dimethyl-propyl]-amide (160 mg, 0.26 mmol) in CH2Cl2 (2.25 mL) was added trifluoroacetic acid (0.75 mL). The reaction mixture was stirred at room temperature for 2 h and concentrated. The residue was dissolved in a mixture of ammonium hydroxide, MeOH and CH2Cl2 (1:10:60, 3.0 mL) and stirred at room temperature for 30 min. The reaction mixture was then concentrated and the residue purified twice by SiO2 chromatography (0-5% MeOH/EtOAc then 0-10% MeOH/CH2Cl2) to afford 27 mg (21%) of 2-(1-cyclopropylmethyl-1H-imidazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(4-cyano-piperidine-1-carbonyl)-2,2-dimethyl-propyl]-amide as a white powder. MS: (M+H)+=489.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in a mixture of ammonium hydroxide, MeOH and CH2Cl2 (1:10:60, 3.0 mL)
  3. stirringstirred at room temperature for 30 min
  4. concentrationThe reaction mixture was then concentrated
  5. customthe residue purified twice by SiO2 chromatography (0-5% MeOH/EtOAc

Sources & evidence

ORD record
ord-b4c56f20f30e4b1e861c723f1fef801b
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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