Trifluoroacetic acid → HCID 73295776, compound

HRID 523005Notes

Reaction equation

HRID 523005 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[C:19]([CH3:24])=[N:20][N:21]([CH3:23])[CH:22]=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[C:19]([CH3:24])=[N:20][N:21]([CH3:23])[CH:22]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90041351HCID 90041351, compound

Product 1

HCID 73295776HCID 73295776, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-tert-butyl-2-(1,3-dimethyl-1H-pyrazol-4-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (89 mg, 194 μmol) in dichloromethane (3 mL) was added trifluoroacetic acid (443 mg, 300 μL, 3.89 mmol) and the mixture stirred at room temperature for 16 h. The mixture was concentrated then re-dissolved in dichloromethane (3 mL), methanol (1.5 mL) and ammonium hydroxide (0.45 mL) and the mixture stirred at room temperature for 2 h. The reaction mixture was concentrated then purified by chromatography (silica, 5-8% methanol in dichloromethane) to give N-tert-butyl-2-(1,3-dimethyl-1H-pyrazol-4-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (40 mg, 122 μmol, 63%) as a light brown solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.13 (s, 1H), 8.44 (s, 1H), 7.91 (s, 1H), 7.87 (d, J=3.2, 1 H), 7.82 (s, 1H), 7.81 (s, 1H), 3.71 (s, 3H), 2.09 (s, 3H), 1.35 (s, 9H); MS (EI/CI) m/z: 328.1 [M+H].

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthen re-dissolved in dichloromethane (3 mL)
  3. stirringmethanol (1.5 mL) and ammonium hydroxide (0.45 mL) and the mixture stirred at room temperature for 2 h
  4. concentrationThe reaction mixture was concentrated
  5. customthen purified by chromatography (silica, 5-8% methanol in dichloromethane)

Sources & evidence

ORD record
ord-0a175830b2334341a63d372c14146181
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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