Hydrochloric Acid → HCID 21200651, compound

HRID 849353Notes

Reaction equation

HRID 849353 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][O:12][C:11]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)([CH2:15][CH2:16]OS(C)(=O)=O)[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(S(O)(=O)=[O:37])C=CC=CC=1.[C:40]1([C:46]2([C:52]([NH:54][N:55]3[CH2:59][CH2:58][CH2:57][CH2:56]3)=[O:53])[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C([O-])([O-])=O.[K+].[K+].[ClH:66]>C(#N)C.CN(C=O)C.CC(C)=O.CCOCC.O>[OH2:8].[OH2:37].[ClH:28].[ClH:66].[C:1]([N:9]1[CH2:14][CH2:13][O:12][C:11]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)([CH2:15][CH2:16][N:49]2[CH2:50][CH2:51][C:46]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)([C:52]([NH:54][N:55]3[CH2:59][CH2:58][CH2:57][CH2:56]3)=[O:53])[CH2:47][CH2:48]2)[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 21200513HCID 21200513, compoundHCID 21200544HCID 21200544, compound

Product 1

HCID 21200651HCID 21200651, compound

Reagents, catalysts & solvents 5

HCID 180AcetoneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1.3 g of the compound obtained in step C of EXAMPLE 43, 1.46 g of 4-phenyl-4-(pyrrolidin-1-ylaminocarbonyl)piperidine benzenesulfonate and 1.17 g of K2CO3 in 5 ml of acetonitrile and 5 ml of DMF is heated at 100° C. for 4 hours. After cooling to RT, the reaction mixture is poured into water and extracted with AcOEt, the organic phase is washed twice with water and with saturated NaCl solution and dried over MgSO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica H using DCM and then a DCM/MeOH mixture (97/3; v/v) as the eluent. The product obtained is dissolved in acetone, a saturated solution of hydrochloric acid in ether is added until the pH is 1, and the precipitate formed is wrung to give 1.01 g of the expected product. M.p.=170-174° C.

Workup

  1. temperatureAfter cooling to RT
  2. extractionextracted with AcOEt
  3. washthe organic phase is washed twice with water and with saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. customthe solvent is evaporated off under vacuum
  6. customThe residue is chromatographed on silica H
  7. customThe product obtained
  8. customthe precipitate formed

Sources & evidence

ORD record
ord-18cf6c9c8b534aa9b07967e8b5517bda
Source dataset
uspto-grants-2000_01
Patent number
US06011154

Reaction notes

Loading…