Trifluoroacetic acid → N-(2-(5-chloro-2-fluorophenyl)pyridin-4-yl)-1H-pyrazolo[4,3-b]pyridin-7-amine

HRID 1522583Notes

Reaction equation

HRID 1522583 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:33])=[C:6]([C:8]2[CH:13]=[C:12]([NH:14][C:15]3[C:16]4[C:17](=[CH:21][N:22](CC5C=CC(OC)=CC=5)[N:23]=4)[N:18]=[CH:19][CH:20]=3)[CH:11]=[CH:10][N:9]=2)[CH:7]=1.C(O)(C(F)(F)F)=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:33])=[C:6]([C:8]2[CH:13]=[C:12]([NH:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[CH:21]=[N:22][NH:23][C:16]=34)[CH:11]=[CH:10][N:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54671159N-(2-(5-chloro-2-fluorophenyl)pyridin-4-yl)-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridin-7-amine

Product 1

HCID 54671064N-(2-(5-chloro-2-fluorophenyl)pyridin-4-yl)-1H-pyrazolo[4,3-b]pyridin-7-amine

Conditions

Temperature
70 °C

Procedure

To a vial containing N-(2-(5-chloro-2-fluorophenyl)pyridin-4-yl)-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridin-7-amine was added 5 mL of neat TFA and the mixture was heated at 70° C. for 3 hours. Cooled to room temperature and concentrated to dryness. The residue was purified by preparative HPLC eluting with a gradient of 10-30% acetonitrile (containing 0.035% TFA) in water (containing 0.05% TFA) using a Sunfire Prep 5 μm C18, 75×30 mm column conditions to give, after drying in vacuo, the title compound as a TFA salt as an off-white solid. 1HNMR (400 MHz, DMSO-d6) δ ppm 7.31-7.60 (4H, m) 7.62 (1H, ddd, J=8.78, 4.11, 2.78 Hz) 7.86 (1H, br. s.) 8.01 (1H, dd, J=6.69, 2.65 Hz) 8.56 (2H, d, J=6.32 Hz) 8.75 (1H, d, J=5.81 Hz) 11.12 (1H, br. s.), MS [M+H] found 340.2.

Workup

  1. temperatureCooled to room temperature
  2. concentrationconcentrated to dryness
  3. customThe residue was purified by preparative HPLC
  4. washeluting with a gradient of 10-30% acetonitrile (containing 0.035% TFA) in water (containing 0.05% TFA)
  5. customto give
  6. customafter drying in vacuo

Sources & evidence

ORD record
ord-d5c4b86039b94d68aaf9362734040fee
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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