Morpholine → HCID 11281828, compound

HRID 1985865Notes

Reaction equation

HRID 1985865 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)=[CH:11][N:10]([CH2:20][CH2:21][C:22](O)=[O:23])[C:9]2=[S:25])=[CH:4][CH:3]=1.[NH:26]1[CH2:31][CH2:30]O[CH2:28][CH2:27]1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)=[CH:11][N:10]([CH2:20][CH2:21][C:22]([N:26]3[CH2:31][CH2:30][CH2:28][CH2:27]3)=[O:23])[C:9]2=[S:25])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 57720839HCID 57720839, compound

Product 1

HCID 11281828HCID 11281828, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(1-(4-chlorophenyl)-5-(4-fluorophenyl)-1,2-dihydro-2-thioxoimidazol-3-yl)propionic acid (1 eq), 1-3-(dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.7 eq) and morpholine (1.7 eq) in THF is stirred overnight at room temperature. The reaction is quenched with water and extracted with ethyl acetate. The organics are dried and concentrated under vacuum. The residue is purified by chromatography on silica to give 3-(1-(4-chlorophenyl)-5-(4-fluorophenyl)-1,2-dihydro-2-thioxoimidazol-3-yl)-1-(pyrrolidin-1-yl)propan-1-one.

Workup

  1. customThe reaction is quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organics are dried
  4. concentrationconcentrated under vacuum
  5. customThe residue is purified by chromatography on silica

Sources & evidence

ORD record
ord-132844b7891e407897ccd7002242bde6
Source dataset
uspto-grants-2009_06
Patent number
US07547717B2

Reaction notes

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