Trifluoroacetic acid → HCID 73295778, compound

HRID 523030Notes

Reaction equation

HRID 523030 reaction equation
[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][C:13]([Cl:24])=[C:14]([NH:17][C:18]3[S: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][C:13]([Cl:24])=[C:14]([NH:17][C:18]3[S: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 90040984HCID 90040984, compound

Product 1

HCID 73295778HCID 73295778, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-tert-butyl-3-chloro-2-(3-methylisothiazol-5-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (40 mg, 80.8 μmol) in dichloromethane (1.5 mL) was added trifluoroacetic acid (184 mg, 124 μL, 1.62 mmol) and the mixture stirred at room temperature for 16 h. The mixture was concentrated then re-dissolved in dichloromethane (1.5 mL), methanol (0.75 mL) and ammonium hydroxide (0.2 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-3-chloro-2-(3-methylisothiazol-5-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (15 mg, 37.0 μmol, 46%) as a dark orange solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.76 (s, 1H), 10.91 (s, 1H), 8.30 (d, J=3.2, 1 H), 7.33 (s, 1H), 7.13 (s, 1H), 2.42 (s, 3H), 1.62 (s, 9H); MS (EI/CI) m/z: 365.0 [M+H].

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthen re-dissolved in dichloromethane (1.5 mL)
  3. stirringmethanol (0.75 mL) and ammonium hydroxide (0.2 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-405f4de967c44570848e02dbcbb99286
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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