Trifluoroacetic acid → HCID 178428271, compound

HRID 522963Notes

Reaction equation

HRID 522963 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[NH: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.CO.[OH-].[NH4+]>[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[NH: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

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178428270HCID 178428270, compound

Product 1

HCID 178428271HCID 178428271, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 14923Ammonium HydroxideSolvent

Procedure

To a solution of N-tert-butyl-2-(3-methyl-1H-pyrazol-5-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (25 mg, 56.4 μmol) in dichloromethane (1 mL) was added trifluoroacetic acid (129 mg, 86.8 μL, 1.13 mmol) and the mixture stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo and the residue obtained diluted with dichloromethane (1 mL), methanol (0.5 mL) and ammonium hydroxide (0.15 mL) and stirred at room temperature for 1 h. Purification by chromatography (silica, 20-50% [10% methanol/dichloromethane/0.5% ammonium hydroxide]/dichloromethane) gave N-tert-butyl-2-(3-methyl-1H-pyrazol-5-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (10 mg, 31.9 μmol, 57%) as a light brown solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.19 (s, 1H), 10.12 (s, 1H), 9.53 (s, 1H), 8.07 (s, 1H), 7.93 (d, J=3.0, 1 H), 7.81 (s, 1H), 6.33 (s, 1H), 2.19 (s, 3H), 1.45 (s, 9H); MS (EI/CI) m/z: 314.1 [M+H].

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue obtained
  3. stirringstirred at room temperature for 1 h
  4. customPurification by chromatography (silica, 20-50% [10% methanol/dichloromethane/0.5% ammonium hydroxide]/dichloromethane)

Sources & evidence

ORD record
ord-efb4b2740a6449928335b7b814f88683
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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