Trifluoroacetic acid → HCID 73295447, compound

HRID 522961Notes

Reaction equation

HRID 522961 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]=[N:22][C:21]([CH3:24])=[CH:20][N:19]=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.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]=[N:22][C:21]([CH3:24])=[CH:20][N:19]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735551HCID 131735551, compound

Product 1

HCID 73295447HCID 73295447, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 14923Ammonium HydroxideSolvent

Procedure

To a solution of N-tert-butyl-2-(5-methylpyrazin-2-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (72 mg, 158 mol) in dichloromethane (2.5 mL) was added trifluoroacetic acid (360 mg, 243 μL, 3.16 mmol) and stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo and the residue obtained diluted with dichloromethane (2.5 mL), methanol (1.2 mL) and ammonium hydroxide (0.35 mL) and the mixture 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-(5-methylpyrazin-2-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (26 mg, 79.9 mol, 51%) as a light green solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.45 (s, 1H), 10.12 (s, 1H), 9.17 (d, J=1.5, 1 H), 8.40 (s, 1H), 8.21 (s, 1H), 8.10 (d, J=3.2, 1 H), 7.73 (s, 1H), 2.42 (s, 3H), 1.46 (s, 9H); MS (EI/CI) m/z: 326.1 [M+H].

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue obtained
  3. stirringthe mixture stirred 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-0cc25d262f204474a6c981f720fb6755
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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