Trifluoroacetic acid → 2-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-8-((4-methoxyazepan-4-yl)methoxy)quinoline

HRID 2035667Notes

Reaction equation

HRID 2035667 reaction equation
[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:20][CH2:21][C:22]4([O:36][CH3:37])[CH2:28][CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]4)[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.FC(F)(F)C(O)=O>C(Cl)Cl>[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:20][CH2:21][C:22]4([O:36][CH3:37])[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86654367tert-Butyl 4-((2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)methyl)-4-methoxyazepane-1-carboxylate

Product 1

HCID 672305252-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-8-((4-methoxyazepan-4-yl)methoxy)quinolineYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-((2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)methyl)-4-methoxyazepane-1-carboxylate (0.040 g, 0.079 mmol) was added to a mixture of trifluoroacetic acid and DCM (1:1) for 30 minutes, and the reaction was concentrated. Ethyl acetate was added and the suspension was filtered through a Waters filter (to remove any errant silica gel), and the filtrate was concentrated. DCM was added followed by precipitation with HCl dissolved in diethyl ether, evaporated, co-evaporated in diethyl ether to yield 16 mgs of the desired product as a yellow solid (95% pure by LC). MS ESI (+) m/z 404 (M+1) detected.

Workup

  1. concentrationthe reaction was concentrated
  2. additionEthyl acetate was added
  3. filtrationthe suspension was filtered through a Waters
  4. filtrationfilter (
  5. customto remove any errant silica gel), and the filtrate
  6. concentrationwas concentrated
  7. additionDCM was added
  8. customfollowed by precipitation with HCl
  9. dissolutiondissolved in diethyl ether
  10. customevaporated, co-evaporated in diethyl ether

Sources & evidence

ORD record
ord-76f6edf45cdb4694817f979ac730eb51
Source dataset
uspto-grants-2013_11
Patent number
US08575145B2

Reaction notes

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