Trifluoroacetic acid → N-tert-butyl-2-(1-methyl-1H-pyrazol-4-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 522955Notes

Reaction equation

HRID 522955 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:19]=[N:20][N:21]([CH3:23])[CH:22]=3)[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>[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:19]=[N:20][N:21]([CH3:23])[CH:22]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735548N-tert-butyl-2-(1-methyl-1H-pyrazol-4-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Product 1

HCID 73295610N-tert-butyl-2-(1-methyl-1H-pyrazol-4-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamideYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-tert-butyl-2-(1-methyl-1H-pyrazol-4-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (89 mg, 201 mol) in dichloromethane (3 mL) was added trifluoroacetic acid (458 mg, 309 μL, 4.01 mmol) and the reaction mixture stirred at room temperature for 16 h. The mixture was concentrated in vacuo then dissolved in dichloromethane (3 mL), methanol (1.5 mL) and ammonium hydroxide (0.45 mL) and the mixture stirred at room temperature for 1 h. After concentration in vacuo, the mixture was triturated with water and filtered to collect the solid. The solid was washed with ether and dried to give N-tert-butyl-2-(1-methyl-1H-pyrazol-4-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (58 mg, 185 mol, 92%) as a brown solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.18 (s, 1H), 9.11 (s, 1H), 7.90 (d, J=3.2, 1 H), 7.86 (s, 1H), 7.85 (s, 1H), 7.72 (s, 1H), 7.55 (s, 1H), 3.80 (s, 3H), 1.43 (s, 9H); MS (EI/CI) m/z: 314.1 [M+H].

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthen dissolved in dichloromethane (3 mL)
  3. stirringmethanol (1.5 mL) and ammonium hydroxide (0.45 mL) and the mixture stirred at room temperature for 1 h
  4. concentrationAfter concentration in vacuo
  5. customthe mixture was triturated with water
  6. filtrationfiltered
  7. customto collect the solid
  8. washThe solid was washed with ether
  9. customdried

Sources & evidence

ORD record
ord-cff5a9113eb6465187d5e13c9861e1a9
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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