Dichloromethane → (R)-tert-Butyl 4-(2-(5-(2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl)piperazine-1-carboxylate

HRID 418540Notes

Reaction equation

HRID 418540 reaction equation
CS(O[CH2:6][C@H:7]([N:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH3:34])[C:15]=2[NH:19][C:20](=[O:33])[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[C:24]([F:32])[CH:23]=2)[C:10]1=[O:35])[CH3:8])(=O)=O.[N:36]1([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.C(N(CC)CC)C.C(Cl)Cl>>[F:32][C:24]1[CH:23]=[C:22]([CH2:21][C:20]([NH:19][C:15]2[C:14]([CH3:34])=[CH:13][CH:12]=[C:11]3[C:16]=2[CH:17]=[CH:18][N:9]([C@H:7]([CH3:8])[CH2:6][N:39]2[CH2:38][CH2:37][N:36]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:41][CH2:40]2)[C:10]3=[O:35])=[O:33])[CH:27]=[CH:26][C:25]=1[C:28]([F:30])([F:31])[F:29]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 59845709(R)-2-(5-(2-(3-Fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl methanesulfonate

Product 1

HCID 66648918(R)-tert-Butyl 4-(2-(5-(2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl)piperazine-1-carboxylateYield 82.7%

Procedure

A mixture of (R)-2-(5-(2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl methanesulfonate (100 mg, 0.0002 mol), tert-butyl 1-piperazinecarboxylate (100 mg, 0.0006 mol), triethylamine (200 mg, 0.002 mol) and methylene chloride (6 mL, 0.09 mol) was stirred at room temperature overnight. The solvents were removed under reduced pressure and the residue was purified by flash chromatography to afford the desired product as a light yellow oil (100 mg, 60%).

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-83de8fdee57d4bc091c9fe5cac01ed9a
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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