Hydrochloric Acid → (R)-2-(3-Fluoro-4-(trifluoromethyl)phenyl)-N-(6-methyl-1-oxo-2-(1-(piperazin-1-yl)propan-2-yl)-1,2-dihydroisoquinolin-5-yl)acetamide

HRID 418541Notes

Reaction equation

HRID 418541 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([NH:15][C:16]2[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]3[C:17]=2[CH:18]=[CH:19][N:20]([C@H:28]([CH3:43])[CH2:29][N:30]2[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]2)[C:21]3=[O:27])=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].CO.Cl.O1CCOCC1>>[F:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([NH:15][C:16]2[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]3[C:17]=2[CH:18]=[CH:19][N:20]([C@H:28]([CH3:43])[CH2:29][N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[C:21]3=[O:27])=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]([F:10])([F:9])[F:11]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 312751,4-DioxaneHCID 66648918(R)-tert-Butyl 4-(2-(5-(2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl)piperazine-1-carboxylate

Product 1

HCID 25014311(R)-2-(3-Fluoro-4-(trifluoromethyl)phenyl)-N-(6-methyl-1-oxo-2-(1-(piperazin-1-yl)propan-2-yl)-1,2-dihydroisoquinolin-5-yl)acetamide

Procedure

To a solution of (R)-tert-butyl 4-(2-(5-(2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl)piperazine-1-carboxylate (100 mg, 0.0002 mol) in methanol (6 mL, 0.1 mol) was added 4M hydrogen chloride in 1,4-dioxane(6 mL, 0.02 mol) at 0° C. The mixture was stirred at room temperature overnight. The volatiles were removed under reduced pressure and the residue was purified by reverse phase preparative HPLC to afford the desired product as a white solid.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-336ad487365a4416b86023af9511be97
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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