Trifluoroacetic acid → HCID 73295780, compound

HRID 523001Notes

Reaction equation

HRID 523001 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][N:21]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[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[CH:23]=[CH:22][N:21]=[C:20]([S:24]([CH3:27])(=[O:25])=[O:26])[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 90041253HCID 90041253, compound

Product 1

HCID 73295780HCID 73295780, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-tert-butyl-2-(2-(methylsulfonyl)pyridin-4-ylamino)-5-((2-(trimethylsilyl) ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (127 mg, 245 μmol) in dichloromethane was added trifluoroacetic acid (558 mg, 377 μL, 4.9 mmol) and the mixture stirred at room temperature for 16 h. The mixture was concentrated then re-dissolved in dichloromethane (4 mL), methanol (2 mL) and ammonium hydroxide (0.7 mL) and the mixture stirred at room temperature for 1 h. The mixture was concentrated in vacuo then triturated with water and filtered. The solid obtained was washed with ether then dried to give N-tert-butyl-2-(2-(methylsulfonyl)pyridin-4-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (94 mg, 242 μmol, 99%) as an off white solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.51 (s, 1H), 10.36 (s, 1H), 8.39 (d, J=5.9, 1 H), 8.10 (s, 1H), 8.01 (s, 1H), 7.99 (dd, J=5.3, 2.3, 1 H), 7.83 (d, J=2.1, 1 H), 7.52 (s, 1H), 3.15 (s, 3H), 1.35 (s, 9H); MS (EI/CI) m/z: 389.1 [M+H].

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthen re-dissolved in dichloromethane (4 mL)
  3. stirringmethanol (2 mL) and ammonium hydroxide (0.7 mL) and the mixture stirred at room temperature for 1 h
  4. concentrationThe mixture was concentrated in vacuo
  5. customthen triturated with water
  6. filtrationfiltered
  7. customThe solid obtained
  8. washwas washed with ether
  9. customthen dried

Sources & evidence

ORD record
ord-e68408e91ebb4eb98ff65792808d64ad
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

Loading…