Trifluoroacetic acid → HCID 178482665, compound

HRID 416712Notes

Reaction equation

HRID 416712 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([Br:20])=[CH:18][N:17]=[C:16]3[NH:21][C:22]([C:24]4[CH:29]=[CH:28][C:27]([N:30]([CH3:32])[CH3:31])=[CH:26][CH:25]=4)=[N:23][C:15]=23)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[Br:20][C:19]1[C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[C:15]2[N:23]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([N:30]([CH3:32])[CH3:31])=[CH:26][CH:25]=3)[NH:21][C:16]2=[N:17][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 178482687HCID 178482687, compound

Product 1

HCID 178482665HCID 178482665, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-[6-Bromo-2-(4-dimethylamino-phenyl)-3H-imidazo[4,5-b]pyridin-7-yl]-piperazine-1-carboxylic acid tert-butyl ester (0.380 g, 0.75 mmol) in dichloromethane (20 mL) at 0° C. was added slowly TFA (2 mL) and the reaction mixture was stirred at rt for 30 mins. TFA (1 mL) was added and the reaction mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo and TFA was co-evaporated with CH3CN. The crude product was run trough a 5 g SCX cartridge and eluted with 0.1M NH3 in methanol. The compound was further triturated in ether/methanol 9/1 to give the title compound as a solid (0.228 g, 75%);

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 1 h
  2. concentrationThe reaction mixture was concentrated in vacuo and TFA
  3. washeluted with 0.1M NH3 in methanol
  4. customThe compound was further triturated in ether/methanol 9/1

Sources & evidence

ORD record
ord-4d4080f3848147be8ec2e855f2964b79
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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