Trifluoroacetic acid → HCID 24851835, compound

HRID 15989Notes

Reaction equation

HRID 15989 reaction equation
FC(F)(F)C(O)=O.[N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH2:18][N:19]3[C:27]4[C:22](=[N:23][CH:24]=[C:25]([C:28]5[CH:49]=[CH:48][C:31]([C:32]([NH:34][CH:35]6[CH2:40][CH2:39][N:38](C(OC(C)(C)C)=O)[CH2:37][CH2:36]6)=[O:33])=[CH:30][CH:29]=5)[N:26]=4)[N:21]=[N:20]3)=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1>C(Cl)Cl>[NH:38]1[CH2:39][CH2:40][CH:35]([NH:34][C:32](=[O:33])[C:31]2[CH:30]=[CH:29][C:28]([C:25]3[N:26]=[C:27]4[N:19]([CH2:18][C:14]5[CH:13]=[C:12]6[C:17](=[CH:16][CH:15]=5)[N:8]=[CH:9][CH:10]=[CH:11]6)[N:20]=[N:21][C:22]4=[N:23][CH:24]=3)=[CH:49][CH:48]=2)[CH2:36][CH2:37]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59341905tert-butyl 4-(4-(3-(quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)benzamido)piperidine-1-carboxylate

Product 1

HCID 24851835HCID 24851835, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.33 mL, 4.2 mmol) was added to a solution of tert-butyl 4-(4-(3-(quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)benzamido)piperidine-1-carboxylate (72 mg, 0.13 mmol) in DCM (1.0 mL). After 96 hours, the reaction was concentrated by rotory evaporation. The residue was purified by prep-HPLC to give N-(piperidin-4-yl)-4-(3-(quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)benzamide (7 mg, yield 25%).

Workup

  1. concentrationthe reaction was concentrated by rotory evaporation
  2. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-0e0a2d6d41f8489b9f7011a2c3d07ee2
Source dataset
uspto-grants-2010_06
Patent number
US07732604B2

Reaction notes

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