Trifluoroacetic acid → HCID 73295608, compound

HRID 522973Notes

Reaction equation

HRID 522973 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:19]=[N:20][N:21]([CH2:23][CH3:24])[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.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[CH:19]=[N:20][N:21]([CH2:23][CH3:24])[CH:22]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735557HCID 131735557, compound

Product 1

HCID 73295608HCID 73295608, compoundYield 56.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 14923Ammonium HydroxideSolvent

Procedure

To a solution of N-tert-butyl-2-(1-ethyl-1H-pyrazol-4-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (82 mg, 179 μmol) in dichloromethane (2.7 mL) was added trifluoroacetic acid (409 mg, 276 μL, 3.58 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 (3 mL), methanol (1.5 mL) and ammonium hydroxide (0.4 mL) and stirred at room temperature for 1 h. The reaction mixture was concentrated then purified by chromatography (silica, 15-65% dichloromethane/[10% dichloromethane/methanol/0.5% ammonium hydroxide]) to give N-tert-butyl-2-(1-ethyl-1H-pyrazol-4-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (33 mg, 101 μmol, 56%) as a yellow solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.16 (s, 1H), 9.06 (s, 1H), 7.90 (d, J=3.3, 1 H), 7.85 (s, 1H), 7.84 (s, 1H), 7.73 (s, 1H), 7.59 (s, 1H), 4.08 (q, J=7.3, 2 H), 1.42 (s, 9H), 1.36 (t, J=7.3, 3 H); MS (EI/CI) m/z: 328.1 [M+H].

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue obtained
  3. stirringstirred at room temperature for 1 h
  4. concentrationThe reaction mixture was concentrated
  5. customthen purified by chromatography (silica, 15-65% dichloromethane/[10% dichloromethane/methanol/0.5% ammonium hydroxide])

Sources & evidence

ORD record
ord-c6fc2e965f854c04be69940241c4ca18
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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