Trifluoroacetic acid → HCID 178434266, compound

HRID 490097Notes

Reaction equation

HRID 490097 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:12]=[N:13][CH:14]=[C:15]([N:17]4[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[C@@H:19]([CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH2:18]4)[N:16]=3)[CH:9]=2)[NH:4][N:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:12]=[N:13][CH:14]=[C:15]([N:17]4[CH2:22][CH2:21][NH:20][C@@H:19]([CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH2:18]4)[N:16]=3)[CH:9]=2)[NH:4][N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178434269HCID 178434269, compound

Product 1

HCID 178434266HCID 178434266, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3-methylindazol-5-yl)-5-[(S)-4-Boc-3-benzylpiperazin-1-yl]-[1,2,4]triazine 124 (0.012 g, 0.025 mmol) was added a solution of trifluoroacetic acid in dichloromethane (20% v/v, 2 mL). The reaction mixture was stirred at room temperature for 1 hour. The organic solvent was evaporated under reduced pressure. Methanol (1 mL) and dichloromethane (9 mL) were added. The organic solvent was evaporated under reduced pressure. The crude product was purified by RP-HPLC to yield the desired 3-(3-methylindazol-5-yl)-5-[(S)-3-benzylpiperazin-1-yl]-[1,2,4]triazine 12 (0.0041 g, 0.0106 mmol).

Workup

  1. customThe organic solvent was evaporated under reduced pressure
  2. additionMethanol (1 mL) and dichloromethane (9 mL) were added
  3. customThe organic solvent was evaporated under reduced pressure
  4. customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-7f18254ecae8441b9e0d8320490213bf
Source dataset
uspto-grants-2009_05
Patent number
US07528132B2

Reaction notes

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