Trifluoroacetic acid → 2-(1-ethyl-1H-pyrazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2,2-dimethyl-1-(pyrrolidine-1-carbonyl)-propyl]-amide

HRID 1898499Notes

Reaction equation

HRID 1898499 reaction equation
[CH3:1][C:2]([CH3:39])([CH3:38])[C@@H:3]([NH:11][C:12]([C:14]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]([C:23]3[CH:24]=[N:25][N:26]([CH2:28][CH3:29])[CH:27]=3)[N:21]=2)[N:16](COCC[Si](C)(C)C)[CH:15]=1)=[O:13])[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]([CH3:38])([CH3:39])[C@@H:3]([NH:11][C:12]([C:14]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]([C:23]3[CH:24]=[N:25][N:26]([CH2:28][CH3:29])[CH:27]=3)[N:21]=2)[NH:16][CH:15]=1)=[O:13])[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 673867412-(1-ethyl-1H-pyrazol-4-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2,2-dimethyl-1-(pyrrolidine-1-carbonyl)-propyl]-amide

Product 1

HCID 533858892-(1-ethyl-1H-pyrazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2,2-dimethyl-1-(pyrrolidine-1-carbonyl)-propyl]-amideYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(1-ethyl-1H-pyrazol-4-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2,2-dimethyl-1-(pyrrolidine-1-carbonyl)-propyl]-amide in CH2Cl2 (2.25 mL) was added TFA (0.75 mL). The reaction mixture was stirred overnight 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 90 min. The reaction mixture was then concentrated and the residue purified by SiO2 chromatography (0-10% MeOH/CH2Cl2) to afford 85 mg (89%) of 2-(1-ethyl-1H-pyrazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2,2-dimethyl-1-(pyrrolidine-1-carbonyl)-propyl]-amide as a yellow powder. MS: (M+H)+=424.

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 90 min
  4. concentrationThe reaction mixture was then concentrated
  5. customthe residue purified by SiO2 chromatography (0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2c126c432827488d989b47952b9da600
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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