Trifluoroacetic acid → HCID 73295950, compound

HRID 522989Notes

Reaction equation

HRID 522989 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[O:22][N:21]=[C:20]([CH3:23])[CH: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>[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[O:22][N:21]=[C:20]([CH3:23])[CH:19]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90041584HCID 90041584, compound

Product 1

HCID 73295950HCID 73295950, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-tert-Butyl-2-(3-methylisoxazol-5-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (33 mg, 74.2 mol) was dissolved in dichloromethane (1.3 mL) and treated with trifluoroacetic acid (169 mg, 114 μL, 1.48 mmol). The mixture was stirred at room temperature for 16 h, then concentrated and re-dissolved in dichloromethane (1.3 mL), methanol (0.65 mL) and ammonium hydroxide (0.2 mL) and stirred at room temperature for 1 h. The mixture was concentrated and diluted with water, triturated and filtered. The solid obtained was washed with ether and dried to give N-tert-butyl-2-(3-methylisoxazol-5-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (16 mg, 45.8 mol, 62%) as a yellow solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.53 (s, 1H), 11.06 (s, 1H), 8.14 (d, J=3.0, 1 H), 8.09 (s, 1H), 7.57 (s, 1H), 6.18 (s, 1H), 2.17 (s, 3H), 1.48 (s, 9H); MS (EI/CI) m/z: 315.1 [M+H].

Workup

  1. concentrationconcentrated
  2. dissolutionre-dissolved in dichloromethane (1.3 mL)
  3. stirringmethanol (0.65 mL) and ammonium hydroxide (0.2 mL) and stirred at room temperature for 1 h
  4. concentrationThe mixture was concentrated
  5. additiondiluted with water
  6. customtriturated
  7. filtrationfiltered
  8. customThe solid obtained
  9. washwas washed with ether
  10. customdried

Sources & evidence

ORD record
ord-83fde1fd84954395af9b303e8bcbc067
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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