Dichloromethane → (R)-2-(5-(2-(3-Fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl methanesulfonate

HRID 418537Notes

Reaction equation

HRID 418537 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:10]=[C:11]([CH2:19][C:20]([NH:22][C:23]2[C:32]([CH3:33])=[CH:31][CH:30]=[C:29]3[C:24]=2[CH:25]=[CH:26][N:27]([C@H:35]([CH3:38])[CH2:36][OH:37])[C:28]3=[O:34])=[O:21])[CH:12]=[CH:13][C:14]=1[C:15]([F:18])([F:17])[F:16].[CH3:39][S:40](Cl)(=[O:42])=[O:41].C(Cl)Cl>CN(C)C1C=CN=CC=1>[CH3:39][S:40]([O:37][CH2:36][C@H:35]([N:27]1[CH:26]=[CH:25][C:24]2[C:29](=[CH:30][CH:31]=[C:32]([CH3:33])[C:23]=2[NH:22][C:20](=[O:21])[CH2:19][C:11]2[CH:12]=[CH:13][C:14]([C:15]([F:18])([F:16])[F:17])=[C:9]([F:8])[CH:10]=2)[C:28]1=[O:34])[CH3:38])(=[O:42])=[O:41]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 25013922(R)-2-(3-fluoro-4-(trifluoromethyl)phenyl)-N-(2-(1-hydroxypropan-2-yl)-6-methyl-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide

Product 1

HCID 59845709(R)-2-(5-(2-(3-Fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Triethylamine (0.2 g, 0.002 mol) was added to a solution of (R)-2-(3-fluoro-4-(trifluoromethyl)phenyl)-N-(2-(1-hydroxypropan-2-yl)-6-methyl-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide (0.5 g, 0.001 mol), methanesulfonyl chloride (0.16 g, 0.0014 mol) and 4-dimethylaminopyridine (10 mg, 0.0001 mol) in methylene chloride (10 mL, 0.2 mol). The mixture was stirred at room temperature overnight. The volatiles were removed under reduced pressure and the mixture was purified via flash chromatography to afford the desired product as a white solid.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe mixture was purified via flash chromatography

Sources & evidence

ORD record
ord-3ff868edc6e84617af4f0b72a5834cb4
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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