Trifluoroacetic acid → HCID 58459334, compound

HRID 2036627Notes

Reaction equation

HRID 2036627 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]1[CH:16]([NH:18]C(=O)OC(C)(C)C)[CH3:17].C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]1[CH:16]([NH2:18])[CH3:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58459262HCID 58459262, compound

Product 1

HCID 58459334HCID 58459334, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl 1-(1-(pyridin-2-yl)-1H-imidazo[4,5-b]pyridin-2-yl)ethylcarbamate (0.516 g, 1.520 mmol) in DCM (10.14 mL) was added TFA (10.14 mL, 132 mmol) dropwise at rt with stirring. After 50 min, the mixture was concentrated in vacuo and co-evaporated with triethylamine and MeOH. The neutralized crude mixture was purified by chromatography through a Redi-Sep™ pre-packed silica gel column (40 g), eluting with a gradient of 0% to 100% DCM:MeOH:NH4OH (89:9:1) in DCM, to provide 1-(1-(pyridin-2-yl)-1H-imidazo[4,5-b]pyridin-2-yl)ethanamine as brown syrup: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.68-8.76 (1H, m), 8.49 (1H, dd, J=4.7, 1.6 Hz), 8.19 (1H, td, J=7.7, 2.0 Hz), 7.79-7.92 (2H, m), 7.63 (1H, ddd, J=7.6, 4.8, 0.9 Hz), 7.32 (1H, dd, J=8.1, 4.8 Hz), 4.47 (1H, q, J=6.7 Hz), 1.45 (3H, d, J=6.8 Hz); LC-MS (ESI) m/z 240.1 [M+H]+.

Workup

  1. concentrationthe mixture was concentrated in vacuo and co-evaporated with triethylamine and MeOH
  2. customThe neutralized crude mixture was purified by chromatography through a Redi-Sep™ pre-packed silica gel column (40 g)
  3. washeluting with a gradient of 0% to 100% DCM:MeOH:NH4OH (89:9:1) in DCM

Sources & evidence

ORD record
ord-ca7a1b88bb7d41cbbf4e76fac0a2191d
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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