Trifluoroacetic acid → HCID 73295775, compound

HRID 523007Notes

Reaction equation

HRID 523007 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[S:22][N:21]=[C:20]([CH3:23])[N: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[S:22][N:21]=[C:20]([CH3:23])[N: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 131735561HCID 131735561, compound

Product 1

HCID 73295775HCID 73295775, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-tert-butyl-2-(3-methyl-1,2,4-thiadiazol-5-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (128 mg, 277 μmol) in dichloromethane (4.3 mL) was added trifluoroacetic acid (632 mg, 427 μL, 5.55 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 (0.6 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-(3-methyl-1,2,4-thiadiazol-5-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (90 mg, 272 μmol, 98%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.80 (s, 1H), 12.57 (s, 1H), 8.35 (s, 1H), 8.34 (s, 1H), 7.34 (s, 1H), 2.53 (s, 3H), 1.62 (s, 9H); MS (EI/CI) m/z: 332.1 [M+H].

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthen re-dissolved in dichloromethane (4 mL)
  3. stirringmethanol (2 mL) and ammonium hydroxide (0.6 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-069c8ef639fa4bc7b4e279832a77b62b
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

Loading…