Hydrochloric Acid → 2-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-6-fluoro-8-(trans-5-fluoroazepan-4-yloxy)quinoline

HRID 876507Notes

Reaction equation

HRID 876507 reaction equation
[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:21][C@H:22]4[C@H:28]([F:29])[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]4)[CH:14]=[C:15]([F:20])[CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.Cl>C(Cl)(Cl)Cl>[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:21][C@H:22]4[C@H:28]([F:29])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)[CH:14]=[C:15]([F:20])[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 313Hydrochloric AcidHCID 131731016trans-Tert-butyl 4-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-8-yloxy)-5-fluoroazepane-1-carboxylate

Product 1

HCID 672336232-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-6-fluoro-8-(trans-5-fluoroazepan-4-yloxy)quinoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Enantiomer 1 of trans-tert-butyl 4-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-8-yloxy)-5-fluoroazepane-1-carboxylate (Peak 1 from Example 91, Step E; 0.210 g, 0.424 mmol) was dissolved in CHCl3 (4.3 mL). To this solution was added HCl (4.24 mL, 17.0 mmol, 4.0M Dioxane) and the mixture was stirred at ambient temperature for 3 hours. The mixture was filtered through a polypropylene filter and washed with CH2Cl2 and Et2O, slurried in hexanes and then dried carefully in vacuo to provide the desired product as white solid. MS ESI (+) m/z 396.1 (M+1) detected.

Workup

  1. filtrationThe mixture was filtered through a polypropylene
  2. filtrationfilter
  3. washwashed with CH2Cl2 and Et2O
  4. customdried carefully in vacuo

Sources & evidence

ORD record
ord-f03207c8ac284623bf6330319413adaf
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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