Morpholine → HCID 178484565, compound

HRID 1820914Notes

Reaction equation

HRID 1820914 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:12][C:13]3[CH:33]=[CH:32][C:31]([C:34]([OH:36])=O)=[CH:30][C:14]=3[C:15]=2[NH:16][C:17]([C@H:19]2[CH2:24][CH2:23][C@H:22]([C:25]([N:27]([CH3:29])[CH3:28])=[O:26])[CH2:21][CH2:20]2)=[O:18])=[O:10])=[N:6][CH:7]=1.[NH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:12][C:13]3[CH:33]=[CH:32][C:31]([C:34]([N:37]4[CH2:42][CH2:41][O:40][CH2:39][CH2:38]4)=[O:36])=[CH:30][C:14]=3[C:15]=2[NH:16][C:17]([C@H:19]2[CH2:24][CH2:23][C@H:22]([C:25]([N:27]([CH3:28])[CH3:29])=[O:26])[CH2:21][CH2:20]2)=[O:18])=[O:10])=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178484566HCID 178484566, compound

Product 1

HCID 178484565HCID 178484565, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 22613685Pyridine--trichloromethane (1/1)Solvent

Procedure

2-{[(5-Chloropyridin-2-yl)amino]carbonyl}-3-[({trans-4-[(dimethylamino)carbonyl]cyclohexyl}carbonyl)amino]-benzofuran-5-carboxylic acid (200 mg) obtained in Example 5 is suspended in chloroform-pyridine (1:3) (8 ml) and thereto are added successively morpholine (68 mg), 1-hydroxybenzotriazole (79 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (112 mg) under ice-cooling. The mixture is then stirred at room temperature for 17 hours. To the reaction solution is poured a saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with chloroform. The organic layer is washed with saturated brine and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the resulting residue is suspended in ethanol-diethyl ether. The precipitates are collected by filtration and dried to give the title compound (174 mg)

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with chloroform
  3. washThe organic layer is washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporating the solvent under reduced pressure
  6. filtrationThe precipitates are collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-f45232cbf6df48c1aaa855fc95653e1f
Source dataset
uspto-grants-2009_10
Patent number
US07605158B2

Reaction notes

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