4-Methylmorpholine → HCID 18446829, compound

HRID 1268825Notes

Reaction equation

HRID 1268825 reaction equation
CN1CCOCC1.[CH3:8][C:9]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:10]=1[N:16]1[CH2:20][CH2:19][CH2:18][S:17]1(=[O:22])=[O:21].[C:23]([C:25]1[CH:26]=[C:27]([NH:31][CH:32]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:33](O)=[O:34])[CH:28]=[CH:29][CH:30]=1)#[N:24].Cl.CN(C)CCCN=C=NCC.O.OC1C2N=NNC=2C=CC=1>CN(C=O)C.O>[C:23]([C:25]1[CH:26]=[C:27]([NH:31][CH:32]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:33]([NH:15][C:13]2[CH:12]=[CH:11][C:10]([N:16]3[CH2:20][CH2:19][CH2:18][S:17]3(=[O:22])=[O:21])=[C:9]([CH3:8])[CH:14]=2)=[O:34])[CH:28]=[CH:29][CH:30]=1)#[N:24]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12042526HCID 12042526, compoundHCID 16642516HCID 16642516, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 18446829HCID 18446829, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

51 μl (0.500 mmol) of 4-methylmorpholine are added to a solution of 113 mg (0.500 mmol) of 2-(2-methyl-4-aminophenyl)isothiazolidine 1,1-dioxide, 126 mg (0.500 mmol) of (3-cyanophenylamino)phenylacetic acid, 96.0 mg (0.500 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (DAPECI) and 68 mg (0.500 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)-N-[4-(1,1-dioxoisothiazolidin-2-yl)-3-methylphenyl]-2-phenylacetamide as a colourless solid; ESI 461.

Workup

  1. filtrationthe precipitate is filtered off

Sources & evidence

ORD record
ord-80d7672332db4e9981d4335988354395
Source dataset
uspto-grants-2007_04
Patent number
US07199133B2

Reaction notes

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