Water → HCID 178505570, compound

HRID 1245003Notes

Reaction equation

HRID 1245003 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH2:12][CH2:11][S:10][CH2:9][CH2:8]1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[NH:21][CH:22]=[C:23]([CH2:31][CH2:32][CH2:33]OS(C3C=CC(C)=CC=3)(=O)=O)[C:24]=2[C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)=[CH:16][CH:15]=1.O>C(#N)C>[F:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[NH:21][CH:22]=[C:23]([CH2:31][CH2:32][CH2:33][SH:10]3[CH2:11][CH2:12][NH:7][CH2:8][CH2:9]3)[C:24]=2[C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67164ThiomorpholineHCID 21922767HCID 21922767, compound

Product 1

HCID 178505570HCID 178505570, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

163 mg (1.18 mmol) of potassium carbonate and 122 μl (1.29 mmol) of thiomorpholine were added to a solution of 450 mg (1.07 mmol) of 2-(4-fluorophenyl)-3-(pyridin-4-yl)-4-[3-(p-toluenesulfonyloxy)propyl]-1H-pyrrole [prepared as described in step 23(iv) above] in 50 ml of acetonitrile. The resulting mixture was heated under reflux overnight. After cooling the reaction mixture to room temperature, water was added and then this was extracted with ethyl acetate. The organic extract was washed with water and then concentrated by evaporation under reduced pressure. The residue thus obtained was purified by chromatography on a silica gel column using a 95:5 by volume mixture of ethyl acetate and methanol as the eluant to give 340 mg (yield 83%) of the title compound as a pale yellow powder.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux overnight
  3. extractionthis was extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by chromatography on a silica gel column
  9. additionby volume mixture of ethyl acetate and methanol as the eluant

Sources & evidence

ORD record
ord-d4b63939bfd34e6783d4fcac215637f2
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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