4-Methylmorpholine → 2-(3-cyanophenylamino)2-(2-fluorophenyl)-N-[3-methyl-4-(2-oxopiperidin-1-yl)phenyl]acetamide

HRID 917580Notes

Reaction equation

HRID 917580 reaction equation
CN1CCOCC1.[C:8]([C:10]1[CH:11]=[C:12]([NH:16][CH:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[F:27])[C:18]([OH:20])=O)[CH:13]=[CH:14][CH:15]=1)#[N:9].[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([N:35]2[CH2:40][CH2:39][CH2:38][CH2:37][C:36]2=[O:41])=[C:31]([CH3:42])[CH:30]=1.Cl.CN(C)CCCN=C=NCC.O.OC1C2N=NNC=2C=CC=1>CN(C=O)C.O>[C:8]([C:10]1[CH:11]=[C:12]([NH:16][CH:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[F:27])[C:18]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][C:36]3=[O:41])=[C:31]([CH3:42])[CH:30]=2)=[O:20])[CH:13]=[CH:14][CH:15]=1)#[N:9]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 115575081-(4-Amino-2-methylphenyl)piperidin-2-oneHCID 58962742(3-Cyanophenylamino)-2-fluorophenylacetic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 589627462-(3-cyanophenylamino)2-(2-fluorophenyl)-N-[3-methyl-4-(2-oxopiperidin-1-yl)phenyl]acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

225 μl (2.22 mmol) of 4-methylmorpholine are added to a solution of 600 mg (2.22 mmol) of (3-cyanophenylamino)-2-fluorophenylacetic acid, 453 mg (2.22 mmol) of 1-(4-amino-2-methylphenyl)piperidin-2-one, 426 mg (2.22 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (DAPECI) and 300 mg (2.22 mmol) of hydroxybenzotriazole hydrate (HOBt) in 1 ml of DMF, and the mixture is stirred at room temperature for 24 hours. The reaction mixture is introduced into water, and the precipitate is filtered off, giving 2-(3-cyanophenylamino)-2-(2-fluorophenyl)-N-[3-methyl-4-(2-oxopiperidin-1-yl)phenyl]acetamide as a colourless solid; ESI 456.

Workup

  1. filtrationthe precipitate is filtered off

Sources & evidence

ORD record
ord-110639b42a3b4139b5c4a2e67e6af96f
Source dataset
uspto-grants-2007_09
Patent number
US07273867B2

Reaction notes

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