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

HRID 418539Notes

Reaction equation

HRID 418539 reaction equation
[CH2:1]([N:4](C)[CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:33])[C:14]=2[NH:18][C:19](=[O:32])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[C:23]([F:31])[CH:22]=2)[C:9]1=[O:34])[CH3:7])C=C.C(Cl)Cl.CN1C(=O)CC(=O)N(C)C1=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:31][C:23]1[CH:22]=[C:21]([CH2:20][C:19]([NH:18][C:14]2[C:13]([CH3:33])=[CH:12][CH:11]=[C:10]3[C:15]=2[CH:16]=[CH:17][N:8]([C@H:6]([CH3:7])[CH2:5][NH:4][CH3:1])[C:9]3=[O:34])=[O:32])[CH:26]=[CH:25][C:24]=1[C:27]([F:30])([F:28])[F:29]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 69860Dimethylbarbituric acidHCID 59845711(R)-N-(2-(1-(Allyl(methyl)amino)propan-2-yl)-6-methyl-1-oxo-1,2-dihydroisoquinolin-5-yl)-2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamide

Product 1

HCID 25014312(R)-2-(3-Fluoro-4-(trifluoromethyl)phenyl)-N-(6-methyl-2-(1-(methylamino)propan-2-yl)-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A solution of (R)—N-(2-(1-(allyl(methyl)amino)propan-2-yl)-6-methyl-1-oxo-1,2-dihydroisoquinolin-5-yl)-2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamide (56 mg, 0.00011 mol) in methylene chloride (2.5 mL, 0.039 mol) was added to 1,3-dimethylbarbituric acid (60 mg, 0.0004 mol) and tetrakis(triphenylphosphine)palladium(0) (1 mg, 0.000001 mol) under argon. The mixture was stirred at room temperature for 4 hours, purified via flash chromatography and then by reverse phase preparative HPLC to afford the desired product as a white solid.

Workup

  1. custompurified via flash chromatography

Sources & evidence

ORD record
ord-dd20fc13a9504c67b400bd0198d177b9
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

Loading…