Trifluoroacetic acid → [8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(3-piperazin-1-yl-phenyl)-amine

HRID 1889938Notes

Reaction equation

HRID 1889938 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]3[N:39]=[C:24]4[C:25]([C:29]5[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=5)=[CH:26][CH:27]=[CH:28][N:23]4[N:22]=3)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:38][S:35]([C:32]1[CH:33]=[CH:34][C:29]([C:25]2[C:24]3[N:23]([N:22]=[C:21]([NH:20][C:16]4[CH:17]=[CH:18][CH:19]=[C:14]([N:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)[CH:15]=4)[N:39]=3)[CH:28]=[CH:27][CH:26]=2)=[CH:30][CH:31]=1)(=[O:36])=[O:37]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 596124154-{3-[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59612339[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(3-piperazin-1-yl-phenyl)-amine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 10340Sodium CarbonateSolvent

Procedure

To a solution of 4-{3-[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester (250.0 mg, 0.4556 mmol) in dichloromethane (1 mL) was added dropwise trifluoroacetic acid (0.40 mL, 5.2 mmol) and the mixture was stirred at room temperature for 6 hours. The mixture was diluted with dichloromethane (20 mL) and saturated aqueous sodium carbonate (10 mL) was added dropwise. The mixture was stirred for 30 minutes. The layers were separated and the aqueous was washed with dichloromethane (3×10 mL). The combined organic layers were dried over magnesium sulfate, filtered and evaporated under reduced pressure. [8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(3-piperazin-1-yl-phenyl)-amine was isolated as a yellow foam (0.168 g, 82%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.49 (d, J=6.7 Hz, 1H), 8.25 (d, J=8.4 Hz, 2H), 8.08 (d, J=8.4 Hz, 2H), 7.65 (d, J=7.2 Hz, 1H), 7.36 (s, 1H), 7.23 (t, J=8.3 Hz, 1H), 7.04-6.96 (m, 2H), 6.86 (s, 1H), 6.60 (d, J=8.3 Hz, 1H), 3.24-3.19 (m, 4H), 3.10 (s, 3H), 3.09-3.04 (m, 4H). MS=449 (MH)+.

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred for 30 minutes
  3. customThe layers were separated
  4. washthe aqueous was washed with dichloromethane (3×10 mL)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8ecf9875d72f46cea07b7be996b2dad8
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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