Trifluoromethanesulfonic acid → HCID 86683222, compound

HRID 1852149Notes

Reaction equation

HRID 1852149 reaction equation
OS(C(F)(F)F)(=O)=O.[CH2:9]([N:16]([CH3:30])[C:17]1[N:18]=[C:19]([Cl:29])[C:20]2[C:25]([CH:26]=1)=[CH:24][C:23]([O:27][CH3:28])=[CH:22][CH:21]=2)[C:10]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:29][C:19]1[C:20]2[C:25](=[CH:24][C:23]([O:27][CH3:28])=[CH:22][CH:21]=2)[CH:26]=[C:17]([N:16]([CH2:9][CH3:10])[CH3:30])[N:18]=1.[Cl:29][C:19]1[C:20]2[C:25](=[CH:24][C:23]([O:27][CH3:28])=[CH:22][CH:21]=2)[CH:26]=[C:17]([NH:16][CH3:9])[N:18]=1

Participants

6

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 86683220HCID 86683220, compound

Product 2

HCID 86683221HCID 86683221, compoundHCID 86683222HCID 86683222, compoundYield 119.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triflic acid (4.09 mL, 46.0 mmol) was added to a solution of N-benzyl-1-chloro-6-methoxy-N-methylisoquinolin-3-amine (1.44 g, 4.60 mmol) in DCM (20 mL) at RT and stirred for 1 hr at RT before reverse adding to a solution of sat. sodium bicarbonate. The organic layer was diluted with DCM and separated. The organic layer was dried over MgSO4, filtered and evaporated. The crude material was purified via silica gel chromatography (90 g column, 0-30% EtOAc:Hex) to give the expected product 1-chloro-6-methoxy-N-methylisoquinolin-3-amine (610 mg, 2.74 mmol, 59.5% yield) as an orange solid. MS: MS m/z 223.15(M++1).

Workup

  1. customseparated
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude material was purified via silica gel chromatography (90 g column, 0-30% EtOAc:Hex)

Sources & evidence

ORD record
ord-1f130054a6ce40c890855e4798dfa9e3
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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