Trifluoroacetic acid → HCID 73295614, compound

HRID 522985Notes

Reaction equation

HRID 522985 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][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][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:19]=[CH:20][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][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 90041581HCID 90041581, compound

Product 1

HCID 73295614HCID 73295614, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-tert-butyl-2-(4-(methylsulfonyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (90 mg, 174 μmol) was dissolved in dichloromethane (3 mL) and treated with trifluoroacetic acid (396 mg, 268 μL, 3.48 mmol). After stirring at room temperature for 16 h, the mixture was concentrated in vacuo then re-dissolved in dichloromethane (3 mL), methanol (1.5 mL) and ammonium hydroxide (0.35 mL) and the mixture stirred at room temperature for 1 h. The mixture was concentrated in vacuo then diluted with water, triturated and filtered. The solid obtained was washed with ether then dried to give N-tert-butyl-2-(4-(methylsulfonyl)phenylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (65 mg, 168 μmol, 97%) as a yellow solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.55 (s, 1H), 10.12 (s, 1H), 8.19 (d, J=2.8, 1 H), 8.16 (s, 1H), 7.95 (d, J=8.8, 2 H), 7.88 (d, J=8.8, 2 H), 7.75 (s, 1H), 3.22 (s, 3H), 1.54 (s, 9H); MS (EI/CI) m/z: 388.2 [M+H].

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionthen re-dissolved in dichloromethane (3 mL)
  3. stirringmethanol (1.5 mL) and ammonium hydroxide (0.35 mL) and the mixture stirred at room temperature for 1 h
  4. concentrationThe mixture was concentrated in vacuo
  5. additionthen diluted with water
  6. customtriturated
  7. filtrationfiltered
  8. customThe solid obtained
  9. washwas washed with ether
  10. customthen dried

Sources & evidence

ORD record
ord-5bd901e5a9d846b8bfcd770df0dccc70
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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