4-Methylmorpholine → HCID 136353921, compound

HRID 2243221Notes

Reaction equation

HRID 2243221 reaction equation
Cl.C[N:3](C)[CH2:4][CH2:5][CH2:6]N=C=NCC.[CH3:13][C:14]1[NH:18][C:17](=[O:19])[N:16]([C:20]2[CH:25]=[CH:24][C:23]([S:26][C:27]3[CH:28]=[C:29]([C:33]4([C:39]([OH:41])=O)[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[CH:30]=[CH:31][CH:32]=3)=[CH:22][CH:21]=2)[N:15]=1.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.C(N)C#C>ClCCl.CN(C)C=O>[CH3:13][C:14]1[NH:18][C:17](=[O:19])[N:16]([C:20]2[CH:25]=[CH:24][C:23]([S:26][C:27]3[CH:28]=[C:29]([C:33]4([C:39]([NH:3][CH2:4][C:5]#[CH:6])=[O:41])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[CH:30]=[CH:31][CH:32]=3)=[CH:22][CH:21]=2)[N:15]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 239041PropargylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136389307HCID 136389307, compound

Product 1

HCID 136353921HCID 136353921, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCL HCl) (1.0 mmol) is added to a mixture of 4-(3-{[4-(3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)phenyl]thio}phenyl)tetrahydro-2H-pyran-4-carboxylic acid (1.0 mmol) (example 15), 1-hydroxybenzotriazole (1.0 mmol), N-methylmorpholine (1.65 mmol) and propargylamine (1.0 mmol) in dichloromethane-dimethylformamide (1:1) at 0° C. The solution is stirred overnight at room temperature, washed with water and the aqueous layer is extracted with dichloromethane. The combined organic extracts are dried with sodium sulphate, filtered and the solvent is evaporated under reduced pressure. The residue is purified by column chromatography over silica gel to yield the title product.

Workup

  1. washwashed with water
  2. extractionthe aqueous layer is extracted with dichloromethane
  3. dry with materialThe combined organic extracts are dried with sodium sulphate
  4. filtrationfiltered
  5. customthe solvent is evaporated under reduced pressure
  6. customThe residue is purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-b71ed0a4461244009c353f52b2cf46eb
Source dataset
uspto-grants-2010_03
Patent number
US07674811B2

Reaction notes

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