Trifluoroacetic acid → 1-(3-(8-(4-(Aminomethyl)piperidin-1-yl)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl)ethane-1,2-diol

HRID 1041972Notes

Reaction equation

HRID 1041972 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][N:8]2[C:11]([C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[C:17]([N:24]5[CH2:29][CH2:28][CH:27]([CH2:30][NH:31]C(=O)OC(C)(C)C)[CH2:26][CH2:25]5)[CH:18]=[CH:19][CH:20]=4)[N:15]=3)=[N:12][N:13]=[C:7]2[CH:6]=1)[CH2:3][OH:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:31][CH2:30][CH:27]1[CH2:26][CH2:25][N:24]([C:17]2[CH:18]=[CH:19][CH:20]=[C:21]3[C:16]=2[N:15]=[C:14]([C:11]2[N:8]4[CH:9]=[CH:10][C:5]([CH:2]([OH:1])[CH2:3][OH:4])=[CH:6][C:7]4=[N:13][N:12]=2)[CH:23]=[CH:22]3)[CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86654349Tert-butyl (1-(2-(7-(1,2-dihydroxyethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

Product 1

HCID 461789051-(3-(8-(4-(Aminomethyl)piperidin-1-yl)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl)ethane-1,2-diolYield 119.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl (1-(2-(7-(1,2-dihydroxyethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate (2 mg, 0.004 mmol) in DCM (1 mL) was added TFA (0.5 mL). The reaction was then stirred for 1 hour, then concentrated and purified by flash column chromatography (DCM/MeOH/NH4OH 20:1:0.1), affording the final product as a white solid (0.002 g; quantitative yield). MS ESI (+) m/z 419 (M+1) detected.

Workup

  1. concentrationconcentrated
  2. custompurified by flash column chromatography (DCM/MeOH/NH4OH 20:1:0.1)

Sources & evidence

ORD record
ord-6c963e1c0df244b59d89544df157eae6
Source dataset
uspto-grants-2013_10
Patent number
US08557809B2

Reaction notes

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