Trifluoroacetic acid → HCID 73295444, compound

HRID 522967Notes

Reaction equation

HRID 522967 reaction equation
[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=3[F:25])[N:15]=2)[N:10](COCC[Si](C)(C)C)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl.CO.[OH-].[NH4+]>[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=3[F:25])[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735554HCID 131735554, compound

Product 1

HCID 73295444HCID 73295444, compoundYield 92.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 14923Ammonium HydroxideSolvent

Procedure

To a solution of N-tert-butyl-2-(2-fluoro-4-methylphenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (87 mg, 184 μmol) in dichloromethane (3 mL) was added trifluoroacetic acid (421 mg, 284 μL, 3.69 mmol) and the mixture stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo and the residue obtained diluted with dichloromethane (3 mL), methanol (1.5 mL) and ammonium hydroxide (0.4 mL) and stirred at room temperature for 1 h. The mixture was concentrated and triturated with water. The solid was collected by filtration and washed with water and ether to give N-tert-butyl-2-(2-fluoro-4-methylphenylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (58 mg, 170 μmol, 92%) as an off-white solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.27 (s, 1H), 8.97 (s, 1H), 8.10 (s, 1H), 7.96 (d, J=2.3, 1 H), 7.81 (t, J=8.6, 1 H), 7.70 (s, 1H), 7.10 (d, J=12.4, 1 H), 6.95 (d, J=8.0, 1 H), 2.29 (s, 3H), 1.32 (s, 9H); MS (EI/CI) m/z: 342.1 [M+H].

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue obtained
  3. stirringstirred at room temperature for 1 h
  4. concentrationThe mixture was concentrated
  5. customtriturated with water
  6. filtrationThe solid was collected by filtration
  7. washwashed with water and ether

Sources & evidence

ORD record
ord-29a5ad6589f645efb7c0a3719de94ced
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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