Trifluoroacetic acid → HCID 73295781, compound

HRID 522999Notes

Reaction equation

HRID 522999 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]=[C:20]([CH:24]([NH:26]C(=O)OC(C)(C)C)[CH3:25])[CH:21]=[CH:22][CH:23]=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>[NH2:26][CH:24]([C:20]1[CH:19]=[C:18]([NH:17][C:14]2[N:15]=[C:16]3[C:8]([C:6]([NH:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])=[CH:9][NH:10][C:11]3=[N:12][CH:13]=2)[CH:23]=[CH:22][CH:21]=1)[CH3:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735560HCID 131735560, compound

Product 1

HCID 73295781HCID 73295781, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 1-(3-(7-(tert-butylcarbamoyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)ethylcarbamate (150 mg, 257 mol) in dichloromethane (4 mL) was added trifluoroacetic acid (587 mg, 397 μL, 5.15 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 (0.7 mL) and the mixture stirred at room temperature for 1 h. The reaction mixture was concentrated then purified by chromatography (silica, 6-10% methanol/dichloromethane) to give 2-(3-(1-aminoethyl)phenylamino)-N-tert-butyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (64 mg, 182 mol, 71%) as a yellow solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 9.44 (s, 1H), 8.01 (s, 1H), 7.99 (d, J=7.9, 1 H), 7.98 (s, 1H), 7.77 (s, 1H), 7.22 (t, J=7.8, 1 H), 7.20 (s, 1H), 6.98 (d, J=7.8, 1 H), 4.05 (q, J=6.1, 1 H), 1.43 (s, 9H), 1.32 (d, J=6.5, 3 H); MS (EI/CI) m/z: 353.2 [M+H].

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthen re-dissolved in dichloromethane (4 mL)
  3. stirringmethanol (2 mL) and ammonium hydroxide (0.7 mL) and the mixture stirred at room temperature for 1 h
  4. concentrationThe reaction mixture was concentrated
  5. customthen purified by chromatography (silica, 6-10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-b07f4b0e38f64acd841be4bf2ea6e432
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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