Hydrochloric Acid → HCID 58303650, compound

HRID 876416Notes

Reaction equation

HRID 876416 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][CH:21]4[CH:27]([F:28])[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]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.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:20][CH:21]4[CH:27]([F:28])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]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 313Hydrochloric AcidHCID 67231331HCID 67231331, compound

Product 1

HCID 58303650HCID 58303650, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of tert-butyl 4-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-5-fluoroazepane-1-carboxylate (0.157 g, 0.329 mmol) in CHCl3 (3.2 mL) was added HCl (3.29 mL, 13.2 mmol, 4.0 M in dioxane). The mixture was stirred at ambient temperature for 5 hours and was then filtered directly. The solid was washed with CH2Cl2 (5 mL) and Et2O (5 mL) and carefully dried in vacuo to afford the desired product as an off-white solid. The salt was purified directly by column chromatography (10% MeOH/CH2Cl2 with 1% NH3) to provide the free amine product as an off-white solid. MS ESI (+) m/z 378.1 (M+1) detected.

Workup

  1. filtrationwas then filtered directly
  2. washThe solid was washed with CH2Cl2 (5 mL) and Et2O (5 mL)
  3. customcarefully dried in vacuo

Sources & evidence

ORD record
ord-483a28801a2347589e4425312f8d3fe5
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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