Methanol → (R)-2-(3,4-Dichlorophenyl)-N-(2-(1-hydroxypropan-2-yl)-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide

HRID 1161264Notes

Reaction equation

HRID 1161264 reaction equation
C([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[NH2:18])[C:9]1=[O:19])[CH3:7])(=O)C.C(Cl)Cl.[Cl:23][C:24]1[CH:25]=[C:26]([CH2:31][C:32](O)=[O:33])[CH:27]=[CH:28][C:29]=1[Cl:30].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.CO.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:23][C:24]1[CH:25]=[C:26]([CH2:31][C:32]([NH:18][C:14]2[CH:13]=[CH:12][CH:11]=[C:10]3[C:15]=2[CH:16]=[CH:17][N:8]([C@H:6]([CH3:7])[CH2:5][OH:4])[C:9]3=[O:19])=[O:33])[CH:27]=[CH:28][C:29]=1[Cl:30]

Participants

9

Reactant 7

HCID 887MethanolHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 798743,4-Dichlorophenylacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59515825(R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Product 1

HCID 59515701(R)-2-(3,4-Dichlorophenyl)-N-(2-(1-hydroxypropan-2-yl)-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterCatalyst

Procedure

To a solution of (R)-2-(5-amino-1-oxoisoquinolin-2(1H)-yl)propyl acetate (100 mg, 0.0004 mol) in methylene chloride (2 mL, 0.03 mol) was added 3,4-dichlorophenyl acetic acid (120 mg, 0.00058 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (360 mg, 0.00096 mol) and N,N-diisopropylethylamine (300 μL, 0.002 mol). The reaction mixture was stirred overnight at room temperature. The mixture was then purified by column chromatography using an ethyl acetate:hexane (0-40%) gradient. The combined pure fractions were reduced in vacuo and taken up in methanol (3 mL, 0.07 mol), potassium carbonate (200 mg, 0.001 mol) and a few drops of water were added, and the mixture was stirred at room temperature for one hour. This was followed by purification using column chromatography (ethyl acetate:hexane, 0-100%) thus producing the title compound.

Workup

  1. customThe mixture was then purified by column chromatography
  2. stirringthe mixture was stirred at room temperature for one hour
  3. customThis was followed by purification

Sources & evidence

ORD record
ord-fbb837d718d84b379d78ae38d2a888d3
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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