Trifluoroacetic acid → N-(3-ethyl-1-((6-(piperidin-4-yloxy)pyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79307Notes

Reaction equation

HRID 79307 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[N:30]=[C:29]([O:31][CH:32]3[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]3)[CH:28]=[CH:27][CH:26]=2)[N:4]=1)[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[C:29]([O:31][CH:32]3[CH2:33][CH2:34][NH:35][CH2:36][CH2:37]3)[N:30]=2)[N:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67261312tert-butyl 4-(6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yloxy)piperidine-1-carboxylate

Product 1

HCID 67259706N-(3-ethyl-1-((6-(piperidin-4-yloxy)pyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideYield 20.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 4-(6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yloxy)piperidine-1-carboxylate (3 mg, 0.02 mmol) in DCM (1 mL) was added TFA (1 mL). The reaction mixture was stirred for one hour and concentrated. Silica gel chromatography of the crude material (DCM/MeOH/NH4OH 10:1:0.1) provided the desired product (2 mg). MS (ES+APCI) m/z=496 (M+H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-df6b16446f0b4678be58f22aa1c486a6
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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