Morpholine → HCID 59446570, compound

HRID 1510321Notes

Reaction equation

HRID 1510321 reaction equation
Cl[CH2:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([N:14]([CH2:26][P:27](=[O:34])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])[S:15]([C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=3)(=[O:17])=[O:16])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[NH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1.C(OCC)(=O)C>CN(C)C=O.O>[CH2:32]([O:31][P:27]([CH2:26][N:14]([S:15]([C:18]1[CH:19]=[C:20]([Cl:25])[CH:21]=[C:22]([Cl:24])[CH:23]=1)(=[O:17])=[O:16])[C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([C:3](=[O:4])[CH2:2][N:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1)[CH:6]=[CH:7]2)(=[O:34])[O:28][CH2:29][CH3:30])[CH3:33]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 59446538HCID 59446538, compound

Product 1

HCID 59446570HCID 59446570, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

125 mg diethyl {[[1-(2-chloro-acetyl)-1H-indol-5-yl]-(3,5-dichloro-phenylsulphonyl)-amino]-methyl}-phosphonate are dissolved in 2 ml dimethylformamide, combined with 34 mg potassium carbonate and 22 μl morpholine and stirred overnight at ambient temperature. The mixture is divided between ethyl acetate and water. The organic phase is washed with saturated sodium chloride solution and dried on magnesium sulphate. After drying with magnesium sulphate the solvents are eliminated in vacuo and the residue is chromatographed on silica gel (ethyl acetate/methanol 30:1 to 10:1).

Workup

  1. washThe organic phase is washed with saturated sodium chloride solution
  2. customdried on magnesium sulphate
  3. dry with materialAfter drying with magnesium sulphate the solvents
  4. customthe residue is chromatographed on silica gel (ethyl acetate/methanol 30:1 to 10:1)

Sources & evidence

ORD record
ord-66560ea49d8f4e5a8c1b2cd9d07a137b
Source dataset
uspto-grants-2012_07
Patent number
US08211923B2

Reaction notes

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