4-Methylmorpholine → N-[4-(2-oxopiperidin-1-yl)phenyl]-2-(isoquinolin-7-yloxy)pentanamide

HRID 600662Notes

Reaction equation

HRID 600662 reaction equation
CN1CCOCC1.[Na+].[CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH:20]([CH2:24][CH2:25][CH3:26])[C:21]([O-:23])=O)[CH:17]=2)[CH:12]=[CH:11][N:10]=1.[NH2:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH2:39][CH2:38][CH2:37][CH2:36][C:35]2=[O:40])=[CH:30][CH:29]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C=O)C.O>[O:40]=[C:35]1[CH2:36][CH2:37][CH2:38][CH2:39][N:34]1[C:31]1[CH:30]=[CH:29][C:28]([NH:27][C:21](=[O:23])[CH:20]([O:19][C:16]2[CH:17]=[C:18]3[C:13]([CH:12]=[CH:11][N:10]=[CH:9]3)=[CH:14][CH:15]=2)[CH2:24][CH2:25][CH3:26])=[CH:33][CH:32]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 114581781-(4-Aminophenyl)piperidin-2-oneHCID 672684982-(Isoquinolin-7-yloxy)pentanoic acid sodium salt

Product 1

HCID 12044955N-[4-(2-oxopiperidin-1-yl)phenyl]-2-(isoquinolin-7-yloxy)pentanamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

390 ml (3.55 mmol) of 4-methylmorpholine are added to a solution of 940 mg (3.52 mmol) of 2-(isoquinolin-7-yloxy)pentanoic acid sodium salt, 670 mg (3.52 mmol) of 1-(4-aminophenyl)piperidin-2-one, 670 mg (3.52 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (DAPECI) and 480 mg (3.56 mmol) of 1-hydroxybenzotriazole (HOBt) in 2 ml of DMF, and the mixture is stirred at room temperature for 18 hours. The reaction mixture is introduced into water, and the precipitate is filtered off, giving N-[4-(2-oxopiperidin-1-yl)phenyl]-2-(isoquinolin-7-yloxy)pentanamide as a colourless solid; ESI 418.

Workup

  1. filtrationthe precipitate is filtered off

Sources & evidence

ORD record
ord-2e7c36645f224a22b63d6cd31e65209c
Source dataset
uspto-grants-2011_03
Patent number
US07902223B2

Reaction notes

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