Trifluoroacetic acid → HCID 73295779, compound

HRID 523003Notes

Reaction equation

HRID 523003 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][CH:21]=[C:22]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:23]=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][CH:21]=[C:22]([S:24]([CH3:27])(=[O:25])=[O:26])[CH:23]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90041605HCID 90041605, compound

Product 1

HCID 73295779HCID 73295779, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-tert-butyl-2-(5-(methylsulfonyl)pyridin-3-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (125 mg, 241 mol) in dichloromethane was added trifluoroacetic acid (550 mg, 371 μL, 4.82 mmol) and the mixture stirred at room temperature for 16 h. The mixture was concentrated then re-dissolved in dichloromethane (3.7 mL), methanol (1.6 mL) and ammonium hydroxide (0.5 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-(5-(methylsulfonyl)pyridin-3-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (92 mg, 237 mol, 98%) as a yellow solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.38 (s, 1H), 9.90 (s, 1H), 9.40 (d, J=2.5, 1 H), 8.55 (d, J=1.9, 1 H), 8.06 (t, J=2.2, 1H), 8.01 (s, 1H), 7.96 (s, 1H), 7.54 (s, 1H), 3.22 (s, 3H), 1.31 (s, 9H); MS (EI/CI) m/z: 389.1 [M+H].

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthen re-dissolved in dichloromethane (3.7 mL)
  3. stirringmethanol (1.6 mL) and ammonium hydroxide (0.5 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-817fe01e950f487b940bb8b89b0d19bb
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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